Fixes #1961 - S/MIME integration.

2020-06-02 13:01:16 +02:00 · 2020-06-02 13:01:16 +02:00 · 2ffca390a9
commit 2ffca390a9
parent d64ea29efb
117 changed files with 5684 additions and 566 deletions
--- a/7
+++ b/7
@ -38,6 +38,9 @@ gem 'aasm'
 # core - authorization
 gem 'pundit'

+# core - image processing
+gem 'rszr', '0.5.2'
+
 # performance - Memcached
 gem 'dalli'

@ -130,8 +133,8 @@ gem 'autodiscover', git: 'https://github.com/zammad-deps/autodiscover'
 gem 'rubyntlm', git: 'https://github.com/wimm/rubyntlm'
 gem 'viewpoint'

-# image processing
-gem 'rszr', '0.5.2'
+# integrations - S/MIME
+gem 'openssl'

 # Gems used only for develop/test and not required
 # in production environments by default.
--- a/Gemfile.lock
+++ b/Gemfile.lock
@ -355,6 +355,7 @@ GEM
    omniauth-weibo-oauth2 (0.5.2)
      omniauth (~> 1.5)
      omniauth-oauth2 (>= 1.4.0)
+    openssl (2.1.2)
    parallel (1.19.1)
    parser (2.7.1.2)
      ast (~> 2.4.0)
@ -629,6 +630,7 @@ DEPENDENCIES
  omniauth-saml
  omniauth-twitter
  omniauth-weibo-oauth2
+  openssl
  pg (= 0.21.0)
  pre-commit
  pry-rails
--- a/LICENSE-ICONS-3RD-PARTY.json
+++ b/LICENSE-ICONS-3RD-PARTY.json
--- a/app/assets/javascripts/app/controllers/_integration/smime.coffee
+++ b/app/assets/javascripts/app/controllers/_integration/smime.coffee
@ -0,0 +1,258 @@
+class Index extends App.ControllerIntegrationBase
+  featureIntegration: 'smime_integration'
+  featureName: 'S/MIME'
+  featureConfig: 'smime_config'
+  description: [
+    ['S/MIME (Secure/Multipurpose Internet Mail Extensions) is a widely accepted method (or more precisely, a protocol) for sending digitally signed and encrypted messages.']
+  ]
+  events:
+    'change .js-switch input': 'switch'
+
+  render: =>
+    super
+    new Form(
+      el: @$('.js-form')
+    )
+
+    new App.HttpLog(
+      el: @$('.js-log')
+      facility: 'S/MIME'
+    )
+
+class Form extends App.Controller
+  events:
+    'click .js-addCertificate': 'addCertificate'
+    'click .js-addPrivateKey': 'addPrivateKey'
+    'click .js-updateGroup': 'updateGroup'
+
+  constructor: ->
+    super
+    @render()
+
+  currentConfig: ->
+    App.Setting.get('smime_config')
+
+  setConfig: (value) ->
+    App.Setting.set('smime_config', value, {notify: true})
+
+  render: =>
+    @config = @currentConfig()
+
+    @html App.view('integration/smime')(
+      config: @config
+    )
+    @certList()
+    @groupList()
+
+  certList: =>
+    new List(el: @$('.js-certList'))
+
+  groupList: =>
+    new Group(
+      el: @$('.js-groupList')
+      config: @config
+    )
+
+  addCertificate: =>
+    new Certificate(
+      callback: @list
+    )
+
+  addPrivateKey: =>
+    new PrivateKey(
+      callback: @list
+    )
+
+  updateGroup: (e) =>
+    params = App.ControllerForm.params(e)
+    @setConfig(params)
+
+class Certificate extends App.ControllerModal
+  buttonClose: true
+  buttonCancel: true
+  buttonSubmit: 'Add'
+  autoFocusOnFirstInput: false
+  head: 'Add Certificate'
+  large: true
+
+  content: ->
+
+    # show start dialog
+    content = $(App.view('integration/smime_certificate_add')(
+      head: 'Add Certificate'
+    ))
+    content
+
+  onSubmit: (e) =>
+    params = new FormData($(e.currentTarget).closest('form').get(0))
+    params.set('try', true)
+    if _.isEmpty(params.get('data'))
+      params.delete('data')
+    @formDisable(e)
+
+    @ajax(
+      id:          'smime-certificate-add'
+      type:        'POST'
+      url:         "#{@apiPath}/integration/smime/certificate"
+      processData: false
+      contentType: false
+      cache:       false
+      data:        params
+      success:     (data, status, xhr) =>
+        console.log('success')
+        @close()
+        @callback()
+      error: (data) =>
+        console.log('error')
+        @close()
+        details = data.responseJSON || {}
+        @notify
+          type:    'error'
+          msg:     App.i18n.translateContent(details.error_human || details.error || 'Unable to import!')
+          timeout: 6000
+    )
+
+class PrivateKey extends App.ControllerModal
+  buttonClose: true
+  buttonCancel: true
+  buttonSubmit: 'Add'
+  autoFocusOnFirstInput: false
+  head: 'Add Private Key'
+  large: true
+
+  content: ->
+
+    # show start dialog
+    content = $(App.view('integration/smime_private_key_add')(
+      head: 'Add Private Key'
+    ))
+    content
+
+  onSubmit: (e) =>
+    params = new FormData($(e.currentTarget).closest('form').get(0))
+    params.set('try', true)
+    if _.isEmpty(params.get('data'))
+      params.delete('data')
+    @formDisable(e)
+
+    @ajax(
+      id:          'smime-private_key-add'
+      type:        'POST'
+      url:         "#{@apiPath}/integration/smime/private_key"
+      processData: false
+      contentType: false
+      cache:       false
+      data:        params
+      success:     (data, status, xhr) =>
+        @close()
+        @callback()
+      error: (data) =>
+        @close()
+        details = data.responseJSON || {}
+        @notify
+          type:    'error'
+          msg:     App.i18n.translateContent(details.error_human || details.error || 'Unable to import!')
+          timeout: 6000
+    )
+
+
+class List extends App.Controller
+  events:
+    'click .js-remove': 'remove'
+
+  constructor: ->
+    super
+    @load()
+
+  load: =>
+    @ajax(
+      id:    'smime-list'
+      type:  'GET'
+      url:   "#{@apiPath}/integration/smime/certificate"
+      success: (data, status, xhr) =>
+        @render(data)
+
+      error: (data, status) =>
+
+        # do not close window if request is aborted
+        return if status is 'abort'
+
+        details = data.responseJSON || {}
+        @notify(
+          type: 'error'
+          msg:  App.i18n.translateContent(details.error_human || details.error || 'Unable to load list of certificates!')
+        )
+
+        # do something
+    )
+
+  render: (data) =>
+    @html App.view('integration/smime_list')(
+      certs: data
+    )
+
+  remove: (e) =>
+    e.preventDefault()
+    id = $(e.currentTarget).parents('tr').data('id')
+    return if !id
+
+    @ajax(
+      id:    'smime-list'
+      type:  'DELETE'
+      url:   "#{@apiPath}/integration/smime/certificate"
+      data:  JSON.stringify(id: id)
+      success: (data, status, xhr) =>
+        @load()
+
+      error: (data, status) =>
+
+        # do not close window if request is aborted
+        return if status is 'abort'
+
+        details = data.responseJSON || {}
+        @notify(
+          type: 'error'
+          msg:  App.i18n.translateContent(details.error_human || details.error || 'Unable to save!')
+        )
+    )
+
+class Group extends App.Controller
+  constructor: ->
+    super
+    @render()
+
+  render: (data) =>
+    groups = App.Group.search(sortBy: 'name', filter: active: true)
+    @html App.view('integration/smime_group')(
+      groups: groups
+    )
+    for group in groups
+      for type, selector of { default_sign: 'js-signDefault', default_encryption: 'js-encryptionDefault' }
+        selected = true
+        if @config?.group_id && @config.group_id[type]
+          selected = @config.group_id[type][group.id.toString()]
+        selection = App.UiElement.boolean.render(
+          name: "group_id::#{type}::#{group.id}"
+          multiple: false
+          null: false
+          nulloption: false
+          value: selected
+          class: 'form-control--small'
+        )
+        @$("[data-id=#{group.id}] .#{selector}").html(selection)
+
+class State
+  @current: ->
+    App.Setting.get('smime_integration')
+
+App.Config.set(
+  'Integrationsmime'
+  {
+    name: 'S/MIME'
+    target: '#system/integration/smime'
+    description: 'S/MIME enables you to send digitally signed and encrypted messages.'
+    controller: Index
+    state: State
+  }
+  'NavBarIntegrations'
+)
--- a/app/assets/javascripts/app/controllers/_ui_element/ticket_perform_action.coffee
+++ b/app/assets/javascripts/app/controllers/_ui_element/ticket_perform_action.coffee
@ -428,6 +428,35 @@ class App.UiElement.ticket_perform_action

    elementRow.find('.js-setNotification').html(notificationElement).removeClass('hide')

+    if App.Config.get('smime_integration') == true
+      selection = App.UiElement.select.render(
+        name: "#{name}::sign"
+        multiple: false
+        options: {
+          'no': 'Do not sign email'
+          'discard': 'Sign email (if not possible, discard notification)'
+          'always': 'Sign email (if not possible, send notification anyway)'
+        }
+        value: meta.sign
+        translate: true
+      )
+
+      elementRow.find('.js-sign').html(selection)
+
+      selection = App.UiElement.select.render(
+        name: "#{name}::encryption"
+        multiple: false
+        options: {
+          'no': 'Do not encrypt email'
+          'discard': 'Encrypt email (if not possible, discard notification)'
+          'always': 'Encrypt email (if not possible, send notification anyway)'
+        }
+        value: meta.encryption
+        translate: true
+      )
+
+      elementRow.find('.js-encryption').html(selection)
+
  @buildArticleArea: (articleType, elementFull, elementRow, groupAndAttribute, elements, meta, attribute) ->

    return if elementRow.find(".js-setArticle .js-body-#{articleType}").get(0)
--- a/app/assets/javascripts/app/controllers/agent_ticket_create.coffee
+++ b/app/assets/javascripts/app/controllers/agent_ticket_create.coffee
@ -1,11 +1,14 @@
 class App.TicketCreate extends App.Controller
+  @include App.SecurityOptions
+
  elements:
    '.tabsSidebar': 'sidebar'

  events:
-    'click .type-tabs .tab': 'changeFormType'
-    'submit form':           'submit'
-    'click .js-cancel':      'cancel'
+    'click .type-tabs .tab':   'changeFormType'
+    'submit form':             'submit'
+    'click .js-cancel':        'cancel'
+    'click .js-active-toggle': 'toggleButton'

  types: {
    'phone-in': {
@ -121,12 +124,25 @@ class App.TicketCreate extends App.Controller
    # force changing signature
    @$('[name="group_id"]').trigger('change')

+    # add observer to change options
+    @$('[name="cc"], [name="group_id"], [name="customer_id"]').bind('change', =>
+      @updateSecurityOptions()
+    )
+    @updateSecurityOptions()
+
    # show cc
    if type is 'email-out'
      @$('[name="cc"]').closest('.form-group').removeClass('hide')
+
+      if @securityEnabled()
+        @securityOptionsShow()
+
    else
      @$('[name="cc"]').closest('.form-group').addClass('hide')

+      if @securityEnabled()
+        @securityOptionsHide()
+
    # show notice
    @$('.js-note').addClass('hide')
    @$(".js-note[data-type='#{type}']").removeClass('hide')
@ -165,6 +181,13 @@ class App.TicketCreate extends App.Controller
    return false if !diff || _.isEmpty(diff)
    return true

+  updateSecurityOptions: =>
+    params = @params()
+    if params.customer_id_completion
+      params.to = params.customer_id_completion
+
+    @updateSecurityOptionsRemote(@taskKey, params, params, @paramsSecurity())
+
  autosaveStop: =>
    @clearDelay('ticket-create-form-update')
    @el.off('change.local blur.local keyup.local paste.local input.local')
@ -385,6 +408,9 @@ class App.TicketCreate extends App.Controller

    @tokanice()

+  toggleButton: (event) ->
+    @$(event.currentTarget).toggleClass('btn--active')
+
  tokanice: ->
    App.Utils.tokanice('.content.active input[name=cc]', 'email')

@ -447,7 +473,7 @@ class App.TicketCreate extends App.Controller

    # create article
    if sender.name is 'Customer'
-      params['article'] = {
+      params.article = {
        to:           (group && group.name) || ''
        from:         params.customer_id_completion
        cc:           params.cc
@ -459,7 +485,7 @@ class App.TicketCreate extends App.Controller
        content_type: 'text/html'
      }
    else
-      params['article'] = {
+      params.article = {
        from:         (group && group.name) || ''
        to:           params.customer_id_completion
        cc:           params.cc
@ -471,6 +497,11 @@ class App.TicketCreate extends App.Controller
        content_type: 'text/html'
      }

+      # add security params
+      if @securityOptionsShown()
+        params.article.preferences ||= {}
+        params.article.preferences.security = @paramsSecurity()
+
    ticket.load(params)

    ticketErrorsTop = ticket.validate(
--- a/app/assets/javascripts/app/controllers/ticket_zoom.coffee
+++ b/app/assets/javascripts/app/controllers/ticket_zoom.coffee
@ -709,12 +709,11 @@ class App.TicketZoom extends App.Controller
  markFormDiff: (diff = {}) =>
    ticketForm    = @$('.edit')
    ticketSidebar = @$('.tabsSidebar-tab[data-tab="ticket"]')
-    articleForm   = @$('.article-add')
    resetButton   = @$('.js-reset')

    params         = {}
-    params.ticket  = @forRemoveMeta(@formParam(ticketForm))
-    params.article = @forRemoveMeta(@formParam(articleForm))
+    params.ticket  = @forRemoveMeta(@ticketParams())
+    params.article = @forRemoveMeta(@articleNew.params())

    # clear all changes
    if _.isEmpty(diff.ticket) && _.isEmpty(diff.article)
@ -743,6 +742,9 @@ class App.TicketZoom extends App.Controller

      resetButton.removeClass('hide')

+  ticketParams: =>
+    @formParam(@$('.edit'))
+
  submitDisable: (e) =>
    if e
      @formDisable(e)
@ -767,7 +769,7 @@ class App.TicketZoom extends App.Controller
      @submitEnable(e)
      return

-    ticketParams = @formParam(@$('.edit'))
+    ticketParams = @ticketParams()
    articleParams = @articleNew.params()

    # validate ticket
--- a/app/assets/javascripts/app/controllers/ticket_zoom/article_action/email_reply.coffee
+++ b/app/assets/javascripts/app/controllers/ticket_zoom/article_action/email_reply.coffee
@ -253,7 +253,7 @@ class EmailReply extends App.Controller
      icon:       'email'
      attributes: attributes
      internal:   false,
-      features:   ['attachment']
+      features:   ['attachment', 'security']
    }

    articleTypes
--- a/app/assets/javascripts/app/controllers/ticket_zoom/article_new.coffee
+++ b/app/assets/javascripts/app/controllers/ticket_zoom/article_new.coffee
@ -1,4 +1,6 @@
 class App.TicketZoomArticleNew extends App.Controller
+  @include App.SecurityOptions
+
  elements:
    '.js-textarea':                       'textarea'
    '.attachmentPlaceholder':             'attachmentPlaceholder'
@ -24,6 +26,7 @@ class App.TicketZoomArticleNew extends App.Controller
    'click .list-entry-type div':    'changeType'
    'focus .js-textarea':            'openTextarea'
    'input .js-textarea':            'updateLetterCount'
+    'click .js-active-toggle':       'toggleButton'

  constructor: ->
    super
@ -106,6 +109,12 @@ class App.TicketZoomArticleNew extends App.Controller
      @render()
    )

+    # update security options
+    @bind('ui::ticket::updateSecurityOptions', (data) =>
+      return if data.taskKey isnt @taskKey
+      @updateSecurityOptions()
+    )
+
  tokanice: (type = 'email') ->
    App.Utils.tokanice('.content.active .js-to, .js-cc, js-bcc', type)

@ -294,6 +303,11 @@ class App.TicketZoomArticleNew extends App.Controller
            params.body = "#{params.body}\n#{@signature.text()}"
          break

+    # add security params
+    if @securityOptionsShown()
+      params.preferences ||= {}
+      params.preferences.security = @paramsSecurity()
+
    params

  validate: =>
@ -417,6 +431,15 @@ class App.TicketZoomArticleNew extends App.Controller
            @warningTextLength = articleType.warningTextLength
            @delay(@updateLetterCount, 600)
            @$('.js-textSizeLimit').removeClass('hide')
+          if name is 'security'
+            if @securityEnabled()
+              @securityOptionsShow()
+
+              # add observer to change options
+              @$('.js-to, .js-cc').bind('change', =>
+                @updateSecurityOptions()
+              )
+              @updateSecurityOptions()

    # convert remote src images to data uri
    @$('[data-name=body] img').each( (i,image) ->
@ -434,6 +457,9 @@ class App.TicketZoomArticleNew extends App.Controller

    @scrollToBottom() if wasScrolledToBottom

+  updateSecurityOptions: =>
+    @updateSecurityOptionsRemote(@ticket.id, @ui.ticketParams(), @params(), @paramsSecurity())
+
  setArticleTypePost: (type, signaturePosition = 'bottom') =>
    for localConfig in @actions()
      if localConfig && localConfig.setArticleTypePost
@ -625,3 +651,6 @@ class App.TicketZoomArticleNew extends App.Controller
      if localConfig
        actions.push localConfig
    actions
+
+  toggleButton: (event) ->
+    @$(event.currentTarget).toggleClass('btn--active')
--- a/app/assets/javascripts/app/controllers/ticket_zoom/article_view.coffee
+++ b/app/assets/javascripts/app/controllers/ticket_zoom/article_view.coffee
@ -81,11 +81,13 @@ class ArticleViewItem extends App.ObserverController
    '.textBubble-overflowContainer': 'textBubbleOverflowContainer'

  events:
-    'click .textBubble':           'toggleMetaWithDelay'
-    'click .textBubble a':         'stopPropagation'
-    'click .js-toggleFold':        'toggleFold'
-    'click .richtext-content img': 'imageView'
-    'click .attachments img':      'imageView'
+    'click .article-meta-permanent':  'toggleMetaWithDelay'
+    'click .textBubble':              'toggleMetaWithDelay'
+    'click .textBubble a':            'stopPropagation'
+    'click .js-toggleFold':           'toggleFold'
+    'click .richtext-content img':    'imageView'
+    'click .attachments img':         'imageView'
+    'click .js-securityRetryProcess': 'retrySecurityProcess'

  constructor: ->
    super
@ -296,6 +298,46 @@ class ArticleViewItem extends App.ObserverController
    else
      bubbleOverflowContainer.addClass('hide')

+  retrySecurityProcess: (e) ->
+    e.preventDefault()
+    e.stopPropagation()
+
+    article_id = $(e.target).closest('.ticket-article-item').data('id')
+
+    @ajax(
+      id:   'retrySecurityProcess'
+      type: 'POST'
+      url:  "#{@apiPath}/ticket_articles/#{article_id}/retry_security_process"
+      processData: true
+      success: (data, status, xhr) =>
+        if data.sign.success
+          @notify
+            type: 'success'
+            msg:  App.i18n.translateContent('Verify sign success!')
+        else if data.sign.comment
+          comment = App.i18n.translateContent('Verify sign failed!') + ' ' + App.i18n.translateContent(data.sign.comment || '')
+          @notify
+            type: 'error'
+            msg: comment
+            timeout: 2000
+
+        if data.encryption.success
+          @notify
+            type: 'success'
+            msg:  App.i18n.translateContent('Decryption success!')
+        else if data.encryption.comment
+          comment = App.i18n.translateContent('Decryption failed!') + ' ' + App.i18n.translateContent(data.encryption.comment || '')
+          @notify
+            type: 'error'
+            msg:  comment
+            timeout: 2000
+
+      error: (xhr) =>
+        @notify
+          type: 'error'
+          msg:  App.i18n.translateContent('Retry security process failed!')
+    )
+
  stopPropagation: (e) ->
    e.stopPropagation()

--- a/app/assets/javascripts/app/controllers/ticket_zoom/form_handler_security_options.coffee
+++ b/app/assets/javascripts/app/controllers/ticket_zoom/form_handler_security_options.coffee
@ -0,0 +1,10 @@
+class TicketZoomFormHandleSecurityOptions
+
+  # central method, is getting called on every ticket form change
+  # but only trigger event for group_id changes
+  @run: (params, attribute, attributes, classname, form, ui) ->
+
+    return if attribute.name isnt 'group_id'
+    App.Event.trigger('ui::ticket::updateSecurityOptions', { taskKey: ui.taskKey })
+
+App.Config.set('140-ticketFormSecurityOptions', TicketZoomFormHandleSecurityOptions, 'TicketZoomFormHandler')
--- a/app/assets/javascripts/app/lib/mixins/security_options.coffee
+++ b/app/assets/javascripts/app/lib/mixins/security_options.coffee
@ -0,0 +1,89 @@
+# Methods for displaying security ui elements and to get security params
+
+App.SecurityOptions =
+
+  securityOptionsShow: ->
+    @$('.js-securityOptions').removeClass('hide')
+
+  securityOptionsHide: ->
+    @$('.js-securityOptions').addClass('hide')
+
+  securityOptionsShown: ->
+    !@$('.js-securityOptions').hasClass('hide')
+
+  securityEnabled: ->
+    App.Config.get('smime_integration')
+
+  paramsSecurity: =>
+    if @$('.js-securityOptions').hasClass('hide')
+      return {}
+
+    security = {}
+    security.encryption ||= {}
+    security.sign ||= {}
+    security.type = 'S/MIME'
+    if @$('.js-securityEncrypt').hasClass('btn--active')
+      security.encryption.success = true
+    if @$('.js-securitySign').hasClass('btn--active')
+      security.sign.success = true
+    security
+
+  updateSecurityOptionsRemote: (key, ticket, article, securityOptions) ->
+    callback = =>
+      @ajax(
+        id:          "smime-check-#{key}"
+        type:        'POST'
+        url:         "#{@apiPath}/integration/smime"
+        data:        JSON.stringify(ticket: ticket, article: article)
+        processData: true
+        success:     (data, status, xhr) =>
+
+          # get default selected security options
+          selected =
+            encryption: true
+            sign: true
+          smimeConfig = App.Config.get('smime_config')
+          for type, selector of { default_sign: 'sign', default_encryption: 'encryption' }
+            if smimeConfig?.group_id?[type] && ticket.group_id
+              if smimeConfig.group_id[type][ticket.group_id.toString()] == false
+                selected[selector] = false
+
+          @$('.js-securityEncrypt').attr('title', data.encryption.comment)
+
+          # if encryption is possible
+          if data.encryption.success is true
+            @$('.js-securityEncrypt').attr('disabled', false)
+
+            # overrule current selection with Group configuration
+            if selected.encryption
+              @$('.js-securityEncrypt').addClass('btn--active')
+            else
+              @$('.js-securityEncrypt').removeClass('btn--active')
+
+          # if encryption is not possible
+          else
+            @$('.js-securityEncrypt').attr('disabled', true)
+            @$('.js-securityEncrypt').removeClass('btn--active')
+
+          @$('.js-securitySign').attr('title', data.sign.comment)
+
+          # if sign is possible
+          if data.sign.success is true
+            @$('.js-securitySign').attr('disabled', false)
+
+            # overrule current selection with Group configuration
+            if selected.sign
+              @$('.js-securitySign').addClass('btn--active')
+            else
+              @$('.js-securitySign').removeClass('btn--active')
+
+          # if sign is possible
+          else
+            @$('.js-securitySign').attr('disabled', true)
+            @$('.js-securitySign').removeClass('btn--active')
+
+        error: (data) ->
+          details = data.responseJSON || {}
+          console.log(details)
+      )
+    @delay(callback, 200, 'security-check')
--- a/app/assets/javascripts/app/views/agent_ticket_create.jst.eco
+++ b/app/assets/javascripts/app/views/agent_ticket_create.jst.eco
@ -27,10 +27,17 @@
          <form role="form" class="ticket-create">
            <input type="hidden" name="formSenderType"/>
            <input type="hidden" name="form_id" value="<%= @form_id %>"/>
-
            <div class="ticket-form-top"></div>
+            <div class="form-group js-securityOptions hide">
+              <div class="formGroup-label">
+                <label for=""><%- @T('Security') %></label>
+              </div>
+              <div class="horizontal">
+                <div class="btn btn--action js-securityEncrypt js-active-toggle" disabled><%- @Icon('lock-open', 'btn-inactive-icon') %><%- @Icon('lock', 'btn-active-icon') %><%- @T('Encrypt') %></div>
+                <div class="btn btn--action js-securitySign js-active-toggle" disabled><%- @Icon('not-signed', 'btn-inactive-icon') %><%- @Icon('signed', 'btn-active-icon') %><%- @T('Sign') %></div>
+              </div>
+            </div>
            <div class="article-form-top"></div>
-
            <div class="formset-inset">
              <div class="ticket-form-middle horizontal two-columns"></div>
              <div class="ticket-form-bottom"></div>
--- a/app/assets/javascripts/app/views/generic/select.jst.eco
+++ b/app/assets/javascripts/app/views/generic/select.jst.eco
@ -1,5 +1,5 @@
 <div class="controls controls--select">
-  <select id="<%= @attribute.id %>" class="form-control<%= " #{ @attribute.class }" if @attribute.class %>" name="<%= @attribute.name %>" <%= @attribute.multiple %> <%= @attribute.required %> <%= @attribute.autofocus %> <% if @attribute.disabled: %> disabled<% end %>>
+  <select <% if @attribute.id: %>id="<%= @attribute.id %>"<% end %> class="form-control<%= " #{ @attribute.class }" if @attribute.class %>" name="<%= @attribute.name %>" <%= @attribute.multiple %> <%= @attribute.required %> <%= @attribute.autofocus %> <% if @attribute.disabled: %> disabled<% end %>>
 <% if @attribute.options: %>
 <% for row in @attribute.options: %>
    <option value="<%= row.value %>" <%= row.selected %> <%= row.disabled %>><%= row.name %></option>
--- a/app/assets/javascripts/app/views/generic/ticket_perform_action/notification.jst.eco
+++ b/app/assets/javascripts/app/views/generic/ticket_perform_action/notification.jst.eco
@ -24,5 +24,13 @@
  <div class="formGroup-label">
    <label><%- @T('Body') %></label>
  </div>
-  <div class="controls js-body js-body-<%- @notificationType %>"><div class="richtext form-control"><div contenteditable="true" data-name="<%= @name %>::body"><%- @meta.body %></div></div></div>
+  <div class="controls js-body js-body-<%- @notificationType %>">
+    <div class="richtext form-control">
+      <div contenteditable="true" data-name="<%= @name %>::body"><%- @meta.body %></div>
+    </div>
+  </div>
+  <div class="controls js-sign">
+  </div>
+  <div class="controls js-encryption">
+  </div>
 </div>
--- a/app/assets/javascripts/app/views/integration/ldap.jst.eco
+++ b/app/assets/javascripts/app/views/integration/ldap.jst.eco
@ -48,7 +48,7 @@
      <thead><tr><th><%- @T('No Entries') %>
    </table>
  <% else: %>
-    <table class="settings-list" style="width: 100%;">
+    <table class="settings-list settings-list--stretch">
      <thead>
        <tr>
          <th width="40%"><%- @T('LDAP') %>
@ -69,7 +69,7 @@
      <thead><tr><th><%- @T('No Entries') %>
    </table>
  <% else: %>
-    <table class="settings-list" style="width: 100%;">
+    <table class="settings-list settings-list--stretch">
      <thead>
        <tr>
          <th width="40%"><%- @T('LDAP') %>
--- a/app/assets/javascripts/app/views/integration/smime.jst.eco
+++ b/app/assets/javascripts/app/views/integration/smime.jst.eco
@ -0,0 +1,14 @@
+<form>
+  <h2><%- @T('Certificates & Private Keys') %></h2>
+  <div class="settings-entry settings-entry--stretched js-certList"></div>
+
+  <div class="btn btn--primary js-addCertificate"><%- @T('Add Certificate') %></div>
+  <div class="btn js-addPrivateKey"><%- @T('Add Private Key') %></div>
+
+  <hr>
+
+  <h2><%- @T('Default Behavior') %></h2>
+  <p>Choose the default behavior of the S/MIME integration on per group basis. If signing or encrypting is not possible, the setting has no effect. Agents call always manually alter the behavior for each article.</p>
+  <div class="settings-entry settings-entry--stretched js-groupList"></div>
+  <div class="btn btn--primary js-updateGroup"><%- @T('Update') %></div>
+</form>
--- a/app/assets/javascripts/app/views/integration/smime_certificate_add.jst.eco
+++ b/app/assets/javascripts/app/views/integration/smime_certificate_add.jst.eco
@ -0,0 +1,26 @@
+<div>
+<p class="alert alert--danger js-error hide"></p>
+
+<div class="form-group">
+  <div class="formGroup-label">
+    <label for="certificate-upload"><%- @T('Upload Certificate') %></label>
+  </div>
+  <div class="controls">
+    <input name="file" type="file" id="certificate-upload">
+  </div>
+</div>
+
+<div class="or-divider">
+  <span><%- @T('or') %></span>
+</div>
+
+<div class="form-group">
+  <div class="formGroup-label">
+    <label for="certificate-paste"><%- @T('Paste Certificate') %></label>
+  </div>
+  <div class="controls">
+    <textarea cols="25" rows="20" name="data" style="height: 200px;" id="certificate-paste"></textarea>
+  </div>
+</div>
+
+</div>
--- a/app/assets/javascripts/app/views/integration/smime_group.jst.eco
+++ b/app/assets/javascripts/app/views/integration/smime_group.jst.eco
@ -0,0 +1,24 @@
+<table class="settings-list">
+  <thead>
+    <tr>
+      <th width="55%"><%- @T('Group') %>
+      <th><%- @T('Sign') %>
+      <th><%- @T('Encryption') %>
+  </thead>
+  <tbody>
+  <% if _.isEmpty(@groups): %>
+  <tr>
+    <td colspan="6">
+      <%- @T('No Entries') %>
+    </td>
+  </tr>
+  <% else: %>
+    <% for group in @groups: %>
+      <tr data-id="<%= group.id %>">
+        <td><%= group.name %>
+        <td class="js-signDefault">
+        <td class="js-encryptionDefault">
+    <% end %>
+  <% end %>
+  </tbody>
+</table>
--- a/app/assets/javascripts/app/views/integration/smime_list.jst.eco
+++ b/app/assets/javascripts/app/views/integration/smime_list.jst.eco
@ -0,0 +1,34 @@
+<table class="settings-list settings-list--stretch">
+  <thead>
+    <tr>
+      <th width="55%"><%- @T('Subject') %>
+      <th width="10%"><%- @T('Hash') %>
+      <th width="10%"><%- @T('Fingerprint') %>
+      <th width="10%"><%- @T('Created') %>
+      <th width="10%"><%- @T('Expires') %>
+      <th width="5%"><%- @T('Actions') %>
+  </thead>
+  <tbody>
+  <% if _.isEmpty(@certs): %>
+  <tr>
+    <td colspan="6">
+      <%- @T('No Entries') %>
+    </td>
+  </tr>
+  <% else: %>
+    <% for cert in @certs: %>
+      <tr data-id="<%= cert.id %>">
+        <td><%= cert.subject %>
+          <% if cert.private_key: %><br><i><%- @T('Including private key.') %></i><% end %>
+        <td><%= cert.doc_hash %>
+        <td title="<%= cert.fingerprint %>"><%= cert.fingerprint.substr(1, 10) %>...
+        <td><%- @datetime(cert.not_before_at) %>
+        <td><%- @datetime(cert.not_after_at) %>
+        <td>
+         <div class="btn btn--text js-remove" title="<%- @Ti('Remove') %>">
+           <%- @Icon('trash') %>
+         </div>
+    <% end %>
+  <% end %>
+  </tbody>
+</table>
--- a/app/assets/javascripts/app/views/integration/smime_private_key_add.jst.eco
+++ b/app/assets/javascripts/app/views/integration/smime_private_key_add.jst.eco
@ -0,0 +1,37 @@
+<div>
+<p class="alert alert--danger js-error hide"></p>
+
+<div class="form-field-group">
+  <div class="form-group">
+    <div class="formGroup-label">
+      <label for="key-upload"><%- @T('Upload Private Key') %></label>
+    </div>
+    <div class="controls">
+      <input name="file" type="file" id="key-upload">
+    </div>
+  </div>
+
+  <div class="or-divider">
+    <span><%- @T('or') %></span>
+  </div>
+
+  <div class="form-group">
+    <div class="formGroup-label">
+      <label for="key-paste"><%- @T('Paste Private Key') %></label>
+    </div>
+    <div class="controls">
+      <textarea cols="25" rows="20" name="data" style="height: 200px;" id="key-paste"></textarea>
+    </div>
+  </div>
+</div>
+
+<div class="form-group">
+  <div class="formGroup-label">
+    <label for="key-secret"><%- @T('Enter Private Key secret') %></label>
+  </div>
+  <div class="controls">
+    <input class="form-control" name="secret" type="password" id="key-secret">
+  </div>
+</div>
+
+</div>
--- a/app/assets/javascripts/app/views/layout_ref/buttons.jst.eco
+++ b/app/assets/javascripts/app/views/layout_ref/buttons.jst.eco
@ -4,9 +4,10 @@
  <h2>Normal Buttons</h2>
  <h3>Default</h3>
  <div class="btn">Default Button</div>
+  <div class="btn btn--active">Active Button</div>
  <div class="btn btn--slim">Slim Button</div>
-  <div class="btn is-disabled">Disabled Button (via .is-disabled)</div>
-  <div class="btn" disabled>Disabled Button (via [disabled])</div>
+  <div class="btn is-disabled">.is-disabled Button</div>
+  <div class="btn" disabled>[disabled] Button</div>

  <h3>Primary</h3>
  <div class="btn btn--primary">Primary Button</div>
@ -24,6 +25,7 @@
  <div class="horizontal">
    <div class="btn btn--split--first">Split First Button</div>
    <div class="btn btn--split">Split Button</div>
+    <div class="btn btn--split btn--active">Active Split Button</div>
    <div class="btn btn--split--last">Split Last Button</div>
  </div>

--- a/app/assets/javascripts/app/views/ticket_zoom/article_new.jst.eco
+++ b/app/assets/javascripts/app/views/ticket_zoom/article_new.jst.eco
@ -56,6 +56,15 @@
        </div>
        <div class="controls"><input type="text" name="subject" value="<%= @article.subject %>" class="form-control js-mail-inputs2 js-subject"></div>
      </div>
+      <div class="form-group js-securityOptions">
+        <div class="formGroup-label">
+          <label for=""><%- @T('Security') %></label>
+        </div>
+        <div class="horizontal">
+          <div class="btn btn--action js-securityEncrypt js-active-toggle" disabled><%- @Icon('lock-open', 'btn-inactive-icon') %><%- @Icon('lock', 'btn-active-icon') %><%- @T('Encrypt') %></div>
+          <div class="btn btn--action js-securitySign js-active-toggle" disabled><%- @Icon('not-signed', 'btn-inactive-icon') %><%- @Icon('signed', 'btn-active-icon') %><%- @T('Sign') %></div>
+        </div>
+      </div>

      <div class="textBubble js-writeArea">
        <div class="bubble-arrow"></div>
--- a/app/assets/javascripts/app/views/ticket_zoom/article_view.jst.eco
+++ b/app/assets/javascripts/app/views/ticket_zoom/article_view.jst.eco
@ -31,9 +31,51 @@
        <div class="article-meta-value flex contain-text"><%= @article.subject %></div>
      </div>
    <% end %>
+    <% if @article.preferences.security?.encryption?.success || @article.preferences.security?.sign?.success: %>
+      <div class="horizontal article-meta-row">
+        <div class="article-meta-key u-textTruncate"><%- @T('Security') %></div>
+        <div class="article-meta-value flex contain-text">
+          <% if @article.preferences.security?.encryption?.success: %>
+            <span title="<%- @Ti(@article.preferences.security?.encryption?.comment) %>"><%- @Icon('lock', 'article-meta-icon') %> <%- @T('Encrypted') %></span>
+          <% end %>
+          <% if @article.preferences.security?.encryption?.success && @article.preferences.security?.sign?.success: %>
+          ,
+          <% end %>
+          <% if @article.preferences.security?.sign?.success is not null: %>
+            <span title="<%- @Ti(@article.preferences.security?.sign?.comment) %>"><%- @Icon((if @article.preferences.security?.sign?.success is true then 'signed' else 'not-signed'), 'article-meta-icon') %> <%- @T(if @article.preferences.security?.sign?.success is true then 'Signed' else 'Unsigned') %></span>
+          <% end %>
+        </div>
+      </div>
+    <% end %>
    </div>
  </div>
 </div>
+<div class="article-meta-permanent">
+<% if (@article.preferences.security?.sign?.success is false && @article.preferences.security?.sign?.comment) || (@article.preferences.security?.encryption?.success is false && @article.preferences.security?.encryption?.comment): %>
+  <div class="alert alert--warning">
+    <%- @Icon('not-signed') %> <%- @T('Security Error') %>
+    <% if @article.preferences.security?.sign?.success is false && @article.preferences.security?.sign?.comment: %>
+      <br>
+      <%- @T('Sign') %>: <%- @T(@article.preferences.security?.sign?.comment) %>
+    <% end %>
+    <% if @article.preferences.security?.encryption?.success is false && @article.preferences.security?.encryption?.comment: %>
+      <br>
+      <%- @T('Encryption') %>: <%- @T(@article.preferences.security?.encryption?.comment) %>
+    <% end %>
+    <div class="flex-spacer"></div>
+    <div class="btn btn--action btn--small js-securityRetryProcess"><%- @T('Retry security process') %></div>
+  </div>
+<% else if @article.preferences.security?.encryption?.success is true || @article.preferences.security?.sign?.success is true: %>
+  <div class="alert alert--blank horizontal">
+  <% if @article.preferences.security?.encryption?.success is true: %>
+    <span title="<%- @T('Encrypted') %>"><%- @Icon('lock') %></span>
+  <% end %>
+  <% if @article.preferences.security?.sign?.success is true: %>
+    <span title="<%- @T('Signed') %>"><%- @Icon('signed') %></span>
+  <% end %>
+  </div>
+<% end %>
+</div>
 <div class="article-content">
  <% if @article.sender.name isnt 'Agent': %>
  <%    position = 'left' %>
--- a/app/assets/stylesheets/svg-dimensions.css
+++ b/app/assets/stylesheets/svg-dimensions.css
@ -81,6 +81,7 @@
 .icon-mood-superbad { width: 60px; height: 59px; }
 .icon-mood-supergood { width: 60px; height: 59px; }
 .icon-mute { width: 16px; height: 16px; }
+.icon-not-signed { width: 14px; height: 14px; }
 .icon-note { width: 16px; height: 16px; }
 .icon-oauth2-button { width: 29px; height: 24px; }
 .icon-office365-button { width: 29px; height: 24px; }
@ -107,6 +108,7 @@
 .icon-reply { width: 16px; height: 17px; }
 .icon-report { width: 20px; height: 20px; }
 .icon-searchdetail { width: 18px; height: 14px; }
+.icon-signed { width: 14px; height: 14px; }
 .icon-signout { width: 15px; height: 19px; }
 .icon-small-dot { width: 16px; height: 16px; }
 .icon-sms { width: 17px; height: 17px; }
--- a/app/assets/stylesheets/zammad.scss
+++ b/app/assets/stylesheets/zammad.scss
@ -155,7 +155,6 @@ a {

  &.is-disabled,
  &[disabled] {
-    pointer-events: none;
    cursor: not-allowed !important;
    opacity: .33;
  }
@ -443,7 +442,6 @@ pre code.hljs {
  &.is-disabled,
  &[disabled],
  &:disabled {
-    pointer-events: none;
    cursor: not-allowed;
    opacity: .33;
  }
@ -492,20 +490,32 @@ pre code.hljs {
    }

    &.btn--small {
-      height: 27px;
+      height: 26px;
      font-size: 11px;
      padding-left: 8px;
      padding-right: 8px;
    }
  }

+  &-active-icon {
+    display: none;
+  }
+
  &--active {
-    background: hsla(0,0%,0%,.5);
+    background: hsl(204,7%,28%);
    color: white;
    
    &:active {
      background: hsla(0,0%,0%,.55);
    }
+    
+    .btn-inactive-icon {
+      display: none;
+    }
+
+    .btn-active-icon {
+      display: inline;
+    }
  }

  // used in .recipientList-controls
@ -531,9 +541,11 @@ pre code.hljs {
  &--primary {
    color: white;
    background: hsl(203,65%,55%);
+    
    &:active {
      background: hsl(203,65%,45%);
    }
+
    .icon {
      fill: white;
      opacity: 1;
@ -1543,7 +1555,7 @@ label,
 .checkbox.form-group label,
 .label {
  text-transform: uppercase;
-  color: hsl(198,19%,72%);
+  color: hsl(198,15%,69%);
  display: block;
  font-size: 13px;
  font-weight: normal;
@ -1658,6 +1670,18 @@ https://stackoverflow.com/questions/17408815/fieldset-resizes-wrong-appears-to-h
  fieldset { display: table-cell; }
 }

+.form-field-group {
+  padding: 20px;
+  background: hsl(0,0%,97%);
+  --background: hsl(0,0%,97%);
+  border-radius: 4px;
+  margin-bottom: 16px;
+  
+  > .form-group:last-child {
+    margin-bottom: 0;
+  }
+}
+
 fieldset > .form-group {
  padding: 0 4px;
 }
@ -5660,12 +5684,63 @@ footer {
      vertical-align: top;
      margin: 2px 3px 0 0;
      @include rtl(margin, 2px 0 0 3px);
+      
+      &.icon-lock {
+        margin: 0;
+      }
    }

    .article-meta .text-muted {
      color: #96969b;
    }

+  .article-meta-permanent {
+    margin: 0 55px;
+    
+    + .article-content .textBubble {
+      border-top-left-radius: 0;
+      border-top-right-radius: 0;
+      border-top-width: 0;
+    }
+    
+    .alert {
+      margin-bottom: 0;
+      padding-left: 20px;
+      padding-right: 20px;
+      border-radius: 0;
+      box-shadow: 0 0 0 1px inset hsla(0,0%,0%,.04);
+      
+      &:first-child {
+        border-top-left-radius: 2px;
+        border-top-right-radius: 2px;
+      }
+      
+      &--blank {
+        background: hsl(212,14%,99%);
+        color: hsl(198,16%,70%);
+        
+        .customer.ticket-article-item & {
+          background: hsl(201,43%,96%);
+          border-color: hsl(203,38%,92%);
+        }
+      }
+
+      .icon {
+        fill: currentColor;
+        margin: 2px 6px 0 0;
+        vertical-align: top;
+        width: 14px;
+        height: 14px;
+      }
+
+      .icon-lock {
+        margin-top: 1px;
+        width: 16px;
+        height: 16px;
+      }
+    }
+  }
+
  .internal-border {
    padding: 5px;
    border-radius: 8px;
@ -5775,7 +5850,7 @@ footer {

    .bubble-arrow {
      position: absolute;
-      width: 7px;
+      width: 6px;
      height: 9px;
      left: -6px;
      top: 15px;
@ -5786,7 +5861,7 @@ footer {
      content: "";
      position: absolute;
      top: -1px;
-      left: 2px;
+      left: 1px;
      width: 11px;
      height: 11px;
      background: white;
@ -6724,6 +6799,15 @@ footer {
  &--square {
    border-radius: 0;
  }
+
+  .btn {
+    margin-top: -4px;
+    margin-bottom: -5px;
+    
+    &:last-child {
+      margin-right: -5px;
+    }
+  }
 }

 .tags,
@ -7412,7 +7496,6 @@ footer {
  .dropdown-icon {
    width: 16px;
    height: 16px;
-    opacity: 0.39;
  }

  .dropdown-menu.dropdown-menu--light {
@ -8020,9 +8103,37 @@ footer {
  }
 }

+.or-divider {
+  position: relative;
+  margin: 16px 0;
+  text-align: center;
+  
+  &:before {
+    content: "";
+    position: absolute;
+    left: 0;
+    width: 100%;
+    top: 50%;
+    margin-top: -1px;
+    height: 1px;
+    background: hsla(0,0%,0%,.1);
+  }
+  
+  span {
+    position: relative;
+    background: white;
+    background: var(--background, white);
+    padding: 0 10px;
+  }
+}
+
 .settings-entry {
  margin-bottom: 42px;
  max-width: 700px;
+  
+  &--stretched {
+    max-width: none;
+  }
 }

 .setting-controls {
--- a/app/controllers/integration/smime_controller.rb
+++ b/app/controllers/integration/smime_controller.rb
@ -0,0 +1,154 @@
+# Copyright (C) 2012-2016 Zammad Foundation, http://zammad-foundation.org/
+
+class Integration::SMIMEController < ApplicationController
+  prepend_before_action { authentication_check && authorize! }
+
+  def certificate_list
+    render json: SMIMECertificate.all
+  end
+
+  def certificate_delete
+    SMIMECertificate.find(params[:id]).destroy!
+    render json: {
+      result: 'ok',
+    }
+  end
+
+  def certificate_add
+    string = params[:data]
+    if string.blank? && params[:file].present?
+      string = params[:file].read.force_encoding('utf-8')
+    end
+
+    item = SMIMECertificate.create!(public_key: string)
+
+    render json: {
+      result:   'ok',
+      response: item,
+    }
+  rescue => e
+    unprocessable_entity(e)
+  end
+
+  def private_key_delete
+    SMIMECertificate.find(params[:id]).update!(
+      private_key:        nil,
+      private_key_secret: nil,
+    )
+
+    render json: {
+      result: 'ok',
+    }
+  end
+
+  def private_key_add
+    string = params[:data]
+    if string.blank? && params[:file].present?
+      string = params[:file].read.force_encoding('utf-8')
+    end
+
+    raise "Parameter 'data' or 'file' required." if string.blank?
+
+    private_key = OpenSSL::PKey.read(string, params[:secret])
+    modulus     = private_key.public_key.n.to_s(16)
+
+    certificate = SMIMECertificate.find_by(modulus: modulus)
+
+    raise Exceptions::UnprocessableEntity, 'Unable for find certificate for this private key.' if !certificate
+
+    certificate.update!(private_key: string, private_key_secret: params[:secret])
+
+    render json: {
+      result: 'ok',
+    }
+  rescue => e
+    unprocessable_entity(e)
+  end
+
+  def search
+    result = {
+      type: 'S/MIME',
+    }
+
+    result[:encryption] = article_encryption(params[:article])
+    result[:sign]       = article_sign(params[:ticket])
+
+    render json: result
+  end
+
+  def article_encryption(article)
+    result = {
+      success: false,
+      comment: 'no recipient found',
+    }
+
+    return result if article.blank?
+    return result if article[:to].blank? && article[:cc].blank?
+
+    recipient  = [ article[:to], article[:cc] ].compact.join(',').to_s
+    recipients = []
+    begin
+      list = Mail::AddressList.new(recipient)
+      list.addresses.each do |address|
+        recipients.push address.address
+      end
+    rescue # rubocop:disable Lint/SuppressedException
+    end
+
+    return result if recipients.blank?
+
+    begin
+      certs = SMIMECertificate.for_recipipent_email_addresses!(recipients)
+
+      if certs
+        if certs.any?(&:expired?)
+          result[:success] = false
+          result[:comment] = "certificates found for #{recipients.join(',')} but expired"
+        else
+          result[:success] = true
+          result[:comment] = "certificates found for #{recipients.join(',')}"
+        end
+      end
+    rescue => e
+      result[:comment] = e.message
+    end
+
+    result
+  end
+
+  def article_sign(ticket)
+    result = {
+      success: false,
+      comment: 'certificate not found',
+    }
+
+    return result if ticket.blank? || !ticket[:group_id]
+
+    group = Group.find_by(id: ticket[:group_id])
+    return result if !group
+
+    email_address = group.email_address
+    begin
+      list = Mail::AddressList.new(email_address.email)
+      from = list.addresses.first.to_s
+      cert = SMIMECertificate.for_sender_email_address(from)
+      if cert
+        if cert.expired?
+          result[:success] = false
+          result[:comment] = "certificate for #{email_address.email} found but expired"
+        else
+          result[:success] = true
+          result[:comment] = "certificate for #{email_address.email} found"
+        end
+      else
+        result[:success] = false
+        result[:comment] = "no certificate for #{email_address.email} found"
+      end
+    rescue => e
+      result[:comment] = e.message
+    end
+
+    result
+  end
+
+end
--- a/app/controllers/ticket_articles_controller.rb
+++ b/app/controllers/ticket_articles_controller.rb
@ -263,6 +263,15 @@ class TicketArticlesController < ApplicationController
    render json: result, status: :ok
  end

+  def retry_security_process
+    article = Ticket::Article.find(params[:id])
+    authorize!(article, :update?)
+
+    result = SecureMailing.retry(article)
+
+    render json: result
+  end
+
  private

  def sanitized_disposition
--- a/app/jobs/ticket_article_communicate_email_job.rb
+++ b/app/jobs/ticket_article_communicate_email_job.rb
@ -62,7 +62,8 @@ class TicketArticleCommunicateEmailJob < ApplicationJob
          subject:      subject,
          content_type: record.content_type,
          body:         record.body,
-          attachments:  record.attachments
+          attachments:  record.attachments,
+          security:     record.preferences[:security],
        },
        notification
      )
--- a/app/models/channel/email_build.rb
+++ b/app/models/channel/email_build.rb
@ -3,6 +3,8 @@ module Channel::EmailBuild

 =begin

+generate email
+
  mail = Channel::EmailBuild.build(
    from: 'sender@example.com',
    to: 'recipient@example.com',
@ -10,35 +12,37 @@ module Channel::EmailBuild
    content_type: 'text/plain',
  )

+generate email with S/MIME
+
+  mail = Channel::EmailBuild.build(
+    from: 'sender@example.com',
+    to: 'recipient@example.com',
+    body: 'somebody with some text',
+    content_type: 'text/plain',
+    security: {
+      type: 'S/MIME',
+      encryption: {
+        success: true,
+      },
+      sign: {
+        success: true,
+      },
+    }
+  )
+
 =end

  def self.build(attr, notification = false)
    mail = Mail.new

-    # set organization
-    organization = Setting.get('organization')
-    if organization
-      mail['Organization'] = organization.to_s
-    end
-
-    # notification
-    if notification
-      attr['X-Loop']                   = 'yes'
-      attr['Precedence']               = 'bulk'
-      attr['Auto-Submitted']           = 'auto-generated'
-      attr['X-Auto-Response-Suppress'] = 'All'
-    end
-
-    attr['X-Powered-By'] = 'Zammad - Helpdesk/Support (https://zammad.org/)'
-    attr['X-Mailer'] = 'Zammad Mail Service'
-
    # set headers
    attr.each do |key, value|
      next if key.to_s == 'attachments'
      next if key.to_s == 'body'
      next if key.to_s == 'content_type'
+      next if key.to_s == 'security'

-      mail[key.to_s] = if value && value.class != Array
+      mail[key.to_s] = if value.present? && value.class != Array
                         value.to_s
                       else
                         value
@ -70,6 +74,7 @@ module Channel::EmailBuild
    if !html_alternative && attr[:attachments].blank?
      mail.content_type 'text/plain; charset=UTF-8'
      mail.body attr[:body]
+      SecureMailing.outgoing(mail, attr[:security])
      return mail
    end

@ -119,6 +124,25 @@ module Channel::EmailBuild
        }
      end
    end
+
+    SecureMailing.outgoing(mail, attr[:security])
+
+    # set organization
+    organization = Setting.get('organization')
+    if organization.present?
+      mail['Organization'] = organization.to_s
+    end
+
+    if notification
+      mail['X-Loop']                   = 'yes'
+      mail['Precedence']               = 'bulk'
+      mail['Auto-Submitted']           = 'auto-generated'
+      mail['X-Auto-Response-Suppress'] = 'All'
+    end
+
+    mail['X-Powered-By'] = 'Zammad - Helpdesk/Support (https://zammad.org/)'
+    mail['X-Mailer'] = 'Zammad Mail Service'
+
    mail
  end

--- a/app/models/channel/email_parser.rb
+++ b/app/models/channel/email_parser.rb
@ -87,6 +87,7 @@ class Channel::EmailParser
      headers,
      body,
      self.class.sender_attributes(headers),
+      raw: msg,
    ]
    message_attributes.reduce({}.with_indifferent_access, &:merge)
  end
--- a/app/models/channel/filter/secure_mailing.rb
+++ b/app/models/channel/filter/secure_mailing.rb
@ -0,0 +1,8 @@
+# Copyright (C) 2012-2016 Zammad Foundation, http://zammad-foundation.org/
+
+module Channel::Filter::SecureMailing
+
+  def self.run(_channel, mail)
+    ::SecureMailing.incoming(mail)
+  end
+end
--- a/app/models/smime_certificate.rb
+++ b/app/models/smime_certificate.rb
@ -0,0 +1,99 @@
+# Copyright (C) 2012-2016 Zammad Foundation, http://zammad-foundation.org/
+
+class SMIMECertificate < ApplicationModel
+  validates :fingerprint, uniqueness: true
+
+  def self.parse(raw)
+    OpenSSL::X509::Certificate.new(raw.gsub!(/(?:TRUSTED\s)?(CERTIFICATE---)/, '\1'))
+  end
+
+  # Search for the certificate of the given sender email address
+  #
+  # @example
+  #  certificate = SMIMECertificates.for_sender_email_address('some1@example.com')
+  #  # => #<SMIMECertificate:0x00007fdd4e27eec0...
+  #
+  # @return [SMIMECertificate, nil] The found certificate record or nil
+  def self.for_sender_email_address(address)
+    downcased_address = address.downcase
+    where.not(private_key: nil).find_each.detect do |certificate|
+      certificate.email_addresses.include?(downcased_address)
+    end
+  end
+
+  # Search for certificates of the given recipients email addresses
+  #
+  # @example
+  #  certificates = SMIMECertificates.for_recipipent_email_addresses!(['some1@example.com', 'some2@example.com'])
+  #  # => [#<SMIMECertificate:0x00007fdd4e27eec0...
+  #
+  # @raise [ActiveRecord::RecordNotFound] if there are recipients for which no certificate could be found
+  #
+  # @return [Array<SMIMECertificate>] The found certificate records
+  def self.for_recipipent_email_addresses!(addresses)
+    certificates        = []
+    remaining_addresses = addresses.map(&:downcase)
+    find_each do |certificate|
+
+      # intersection of both lists
+      cerfiticate_for = certificate.email_addresses & remaining_addresses
+      next if cerfiticate_for.blank?
+
+      certificates.push(certificate)
+
+      # subtract found recipient(s)
+      remaining_addresses -= cerfiticate_for
+
+      # end loop if no addresses are remaining
+      break if remaining_addresses.blank?
+    end
+
+    return certificates if remaining_addresses.blank?
+
+    raise ActiveRecord::RecordNotFound, "Can't find S/MIME encryption certificates for: #{remaining_addresses.join(', ')}"
+  end
+
+  def public_key=(string)
+    cert = self.class.parse(string)
+
+    self.subject       = cert.subject
+    self.doc_hash      = cert.subject.hash.to_s(16)
+    self.fingerprint   = OpenSSL::Digest.new('SHA1', cert.to_der).to_s
+    self.modulus       = cert.public_key.n.to_s(16)
+    self.not_before_at = cert.not_before
+    self.not_after_at  = cert.not_after
+    self.raw           = cert.to_s
+  end
+
+  def parsed
+    @parsed ||= self.class.parse(raw)
+  end
+
+  def email_addresses
+    @email_addresses ||= begin
+      subject_alt_name = parsed.extensions.detect { |extension| extension.oid == 'subjectAltName' }
+      if subject_alt_name.blank?
+        warning = <<~TEXT.squish
+          SMIMECertificate with ID #{id} has no subjectAltName
+          extension and therefore no email addresses assigned.
+          This makes it useless in terms of S/MIME. Please check.
+        TEXT
+        Rails.logger.warn warning
+        return []
+      end
+
+      # ["IP Address:192.168.7.23", "IP Address:192.168.7.42", "email:jd@example.com", "email:John.Doe@example.com", "dirName:dir_sect"]
+      entries = subject_alt_name.value.split(/,\s?/)
+      # ["email:jd@example.com", "email:John.Doe@example.com"]
+      email_address_entries = entries.select { |entry| entry.start_with?('email') }
+      # ["jd@example.com", "John.Doe@example.com"]
+      email_address_entries.map! { |entry| entry.split(':')[1] }
+      # ["jd@example.com", "john.doe@example.com"]
+      email_address_entries.map!(&:downcase)
+    end
+  end
+
+  def expired?
+    !Time.zone.now.between?(not_before_at, not_after_at)
+  end
+end
--- a/app/models/ticket.rb
+++ b/app/models/ticket.rb
@ -1498,6 +1498,57 @@ result
      return
    end

+    security = nil
+    if Setting.get('smime_integration')
+      sign       = value['sign'].present? && value['sign'] != 'no'
+      encryption = value['encryption'].present? && value['encryption'] != 'no'
+      security   = {
+        type:       'S/MIME',
+        sign:       {
+          success: false,
+        },
+        encryption: {
+          success: false,
+        },
+      }
+
+      if sign
+        sign_found = false
+        begin
+          list = Mail::AddressList.new(email_address.email)
+          from = list.addresses.first.to_s
+          cert = SMIMECertificate.for_sender_email_address(from)
+          if cert && !cert.expired?
+            sign_found                = true
+            security[:sign][:success] = true
+            security[:sign][:comment] = "certificate for #{email_address.email} found"
+          end
+        rescue # rubocop:disable Lint/SuppressedException
+        end
+
+        if value['sign'] == 'discard' && !sign_found
+          logger.info "Unable to send trigger based notification to #{recipient_string} because of missing group #{group.name} email #{email_address.email} certificate for signing (discarding notification)."
+          return
+        end
+      end
+
+      if encryption
+        certs_found = false
+        begin
+          SMIMECertificate.for_recipipent_email_addresses!(recipients_checked)
+          certs_found                     = true
+          security[:encryption][:success] = true
+          security[:encryption][:comment] = "certificates found for #{recipient_string}"
+        rescue # rubocop:disable Lint/SuppressedException
+        end
+
+        if value['encryption'] == 'discard' && !certs_found
+          logger.info "Unable to send trigger based notification to #{recipient_string} because public certificate is not available for encryption (discarding notification)."
+          return
+        end
+      end
+    end
+
    objects = build_notification_template_objects(article)

    # get subject
@ -1516,6 +1567,12 @@ result

    (body, attachments_inline) = HtmlSanitizer.replace_inline_images(body, id)

+    preferences                  = {}
+    preferences[:perform_origin] = perform_origin
+    if security.present?
+      preferences[:security] = security
+    end
+
    message = Ticket::Article.create(
      ticket_id:     id,
      to:            recipient_string,
@ -1525,9 +1582,7 @@ result
      internal:      value['internal'] || false, # default to public if value was not set
      sender:        Ticket::Article::Sender.find_by(name: 'System'),
      type:          Ticket::Article::Type.find_by(name: 'email'),
-      preferences:   {
-        perform_origin: perform_origin,
-      },
+      preferences:   preferences,
      updated_by_id: 1,
      created_by_id: 1,
    )
--- a/app/models/ticket/article.rb
+++ b/app/models/ticket/article.rb
@ -337,4 +337,5 @@ returns
      o_id:   id,
    )
  end
+
 end
--- a/app/policies/controllers/integration/smime_controller_policy.rb
+++ b/app/policies/controllers/integration/smime_controller_policy.rb
@ -0,0 +1,4 @@
+class Controllers::Integration::SMIMEControllerPolicy < Controllers::ApplicationControllerPolicy
+  permit! :search, to: 'ticket.agent'
+  default_permit!('admin.integration.smime')
+end
--- a/config/initializers/inflections.rb
+++ b/config/initializers/inflections.rb
@ -20,4 +20,5 @@ ActiveSupport::Inflector.inflections(:en) do |inflect|
  # Rails thinks the singularized version of knowledge_bases is knowledge_basis?!
  # see: KnowledgeBase.table_name.singularize
  inflect.singular(/(knowledge_base)s$/i, '\1')
+  inflect.acronym 'SMIME'
 end
--- a/config/routes/integration_smime.rb
+++ b/config/routes/integration_smime.rb
@ -0,0 +1,10 @@
+Zammad::Application.routes.draw do
+  api_path = Rails.configuration.api_path
+
+  match api_path + '/integration/smime',                        to: 'integration/smime#search',                   via: :post
+  match api_path + '/integration/smime/certificate',            to: 'integration/smime#certificate_add',          via: :post
+  match api_path + '/integration/smime/certificate',            to: 'integration/smime#certificate_delete',       via: :delete
+  match api_path + '/integration/smime/certificate',            to: 'integration/smime#certificate_list',         via: :get
+  match api_path + '/integration/smime/private_key',            to: 'integration/smime#private_key_add',          via: :post
+  match api_path + '/integration/smime/private_key',            to: 'integration/smime#private_key_delete',       via: :delete
+end
--- a/config/routes/ticket.rb
+++ b/config/routes/ticket.rb
@ -45,5 +45,5 @@ Zammad::Application.routes.draw do
  match api_path + '/ticket_attachment/:ticket_id/:article_id/:id',  to: 'ticket_articles#attachment',      via: :get
  match api_path + '/ticket_attachment_upload_clone_by_article/:article_id', to: 'ticket_articles#ticket_attachment_upload_clone_by_article', via: :post
  match api_path + '/ticket_article_plain/:id',                      to: 'ticket_articles#article_plain',   via: :get
-
+  match api_path + '/ticket_articles/:id/retry_security_process',    to: 'ticket_articles#retry_security_process', via: :post
 end
--- a/contrib/edit-icon-license-list.php
+++ b/contrib/edit-icon-license-list.php
@ -131,7 +131,7 @@ $imageTypes = '{*.svg}';

 # Set to true if you prefer sorting images by name
 # If set to false, images will be sorted by date
-$sortByImageName = false;
+$sortByImageName = true;

 # Set to false if you want the oldest images to appear first
 # This is only used if images are sorted by date (see above)
--- a/contrib/icon-sprite.sketch
+++ b/contrib/icon-sprite.sketch
--- a/db/migrate/20120101000001_create_base.rb
+++ b/db/migrate/20120101000001_create_base.rb
@ -724,5 +724,21 @@ class CreateBase < ActiveRecord::Migration[4.2]
    end
    add_index :active_job_locks, :lock_key, unique: true
    add_index :active_job_locks, :active_job_id, unique: true
+
+    create_table :smime_certificates do |t|
+      t.string :subject,            limit: 500,  null: false
+      t.string :doc_hash,           limit: 250,  null: false
+      t.string :fingerprint,        limit: 250,  null: false
+      t.string :modulus,            limit: 1024, null: false
+      t.datetime :not_before_at,                 null: true
+      t.datetime :not_after_at,                  null: true
+      t.binary :raw,                limit: 10.megabytes,  null: false
+      t.binary :private_key,        limit: 10.megabytes,  null: true
+      t.string :private_key_secret, limit: 500,  null: true
+      t.timestamps limit: 3, null: false
+    end
+    add_index :smime_certificates, [:fingerprint], unique: true
+    add_index :smime_certificates, [:modulus]
+    add_index :smime_certificates, [:subject]
  end
 end
--- a/db/migrate/20200121000001_smime_support.rb
+++ b/db/migrate/20200121000001_smime_support.rb
@ -0,0 +1,74 @@
+class SMIMESupport < ActiveRecord::Migration[5.2]
+  def up
+
+    # return if it's a new setup
+    return if !Setting.find_by(name: 'system_init_done')
+
+    Setting.create_if_not_exists(
+      title:       'S/MIME integration',
+      name:        'smime_integration',
+      area:        'Integration::Switch',
+      description: 'Defines if S/MIME encryption is enabled or not.',
+      options:     {
+        form: [
+          {
+            display: '',
+            null:    true,
+            name:    'smime_integration',
+            tag:     'boolean',
+            options: {
+              true  => 'yes',
+              false => 'no',
+            },
+          },
+        ],
+      },
+      state:       false,
+      preferences: {
+        prio:           1,
+        authentication: true,
+        permission:     ['admin.integration'],
+      },
+      frontend:    true
+    )
+    Setting.create_if_not_exists(
+      title:       'S/MIME config',
+      name:        'smime_config',
+      area:        'Integration::SMIME',
+      description: 'Defines the S/MIME config.',
+      options:     {},
+      state:       {},
+      preferences: {
+        prio:       2,
+        permission: ['admin.integration'],
+      },
+      frontend:    true,
+    )
+    Setting.create_if_not_exists(
+      title:       'Defines postmaster filter.',
+      name:        '0016_postmaster_filter_smime',
+      area:        'Postmaster::PreFilter',
+      description: 'Defines postmaster filter to handle secure mailing.',
+      options:     {},
+      state:       'Channel::Filter::SecureMailing',
+      frontend:    false
+    )
+
+    create_table :smime_certificates do |t|
+      t.string :subject,            limit: 500,  null: false
+      t.string :doc_hash,           limit: 250,  null: false
+      t.string :fingerprint,        limit: 250,  null: false
+      t.string :modulus,            limit: 1024, null: false
+      t.datetime :not_before_at,                 null: true
+      t.datetime :not_after_at,                  null: true
+      t.binary :raw,                limit: 10.megabytes,  null: false
+      t.binary :private_key,        limit: 10.megabytes,  null: true
+      t.string :private_key_secret, limit: 500,  null: true
+      t.timestamps limit: 3, null: false
+    end
+    add_index :smime_certificates, [:fingerprint], unique: true
+    add_index :smime_certificates, [:modulus]
+    add_index :smime_certificates, [:subject]
+  end
+
+end
--- a/db/seeds/settings.rb
+++ b/db/seeds/settings.rb
@ -3349,6 +3349,15 @@ Setting.create_if_not_exists(
  state:       'Channel::Filter::IdentifySender',
  frontend:    false
 )
+Setting.create_if_not_exists(
+  title:       'Defines postmaster filter.',
+  name:        '0016_postmaster_filter_smime',
+  area:        'Postmaster::PreFilter',
+  description: 'Defines postmaster filter to handle secure mailing.',
+  options:     {},
+  state:       'Channel::Filter::SecureMailing',
+  frontend:    false
+)
 Setting.create_if_not_exists(
  title:       'Defines postmaster filter.',
  name:        '0020_postmaster_filter_auto_response_check',
@ -4549,3 +4558,45 @@ Setting.create_if_not_exists(
  },
  frontend:    true
 )
+
+Setting.create_if_not_exists(
+  title:       'S/MIME integration',
+  name:        'smime_integration',
+  area:        'Integration::Switch',
+  description: 'Defines if S/MIME encryption is enabled or not.',
+  options:     {
+    form: [
+      {
+        display: '',
+        null:    true,
+        name:    'smime_integration',
+        tag:     'boolean',
+        options: {
+          true  => 'yes',
+          false => 'no',
+        },
+      },
+    ],
+  },
+  state:       false,
+  preferences: {
+    prio:           1,
+    authentication: true,
+    permission:     ['admin.integration'],
+  },
+  frontend:    true
+)
+
+Setting.create_if_not_exists(
+  title:       'S/MIME config',
+  name:        'smime_config',
+  area:        'Integration::SMIME',
+  description: 'Defines the S/MIME config.',
+  options:     {},
+  state:       {},
+  preferences: {
+    prio:       2,
+    permission: ['admin.integration'],
+  },
+  frontend:    true,
+)
--- a/lib/secure_mailing.rb
+++ b/lib/secure_mailing.rb
@ -0,0 +1,25 @@
+class SecureMailing
+  include ::Mixin::HasBackends
+
+  def self.incoming(mail)
+    active_backends.each do |backend|
+      "#{backend}::Incoming".constantize.process(mail)
+    end
+  end
+
+  def self.retry(article)
+    active_backends.each do |backend|
+      "#{backend}::Retry".constantize.process(article)
+    end
+  end
+
+  def self.outgoing(mail, security)
+    active_backends.each do |backend|
+      "#{backend}::Outgoing".constantize.process(mail, security)
+    end
+  end
+
+  def self.active_backends
+    backends.select(&:active?)
+  end
+end
--- a/lib/secure_mailing/backend.rb
+++ b/lib/secure_mailing/backend.rb
@ -0,0 +1,9 @@
+class SecureMailing::Backend
+  include Mixin::IsBackend
+
+  def self.inherited(subclass)
+    subclass.is_backend_of(::SecureMailing)
+  end
+end
+
+Mixin::RequiredSubPaths.eager_load_recursive(__dir__)
--- a/lib/secure_mailing/backend/handler.rb
+++ b/lib/secure_mailing/backend/handler.rb
@ -0,0 +1,6 @@
+class SecureMailing::Backend::Handler
+
+  def self.process(*args)
+    new(*args).process
+  end
+end
--- a/lib/secure_mailing/smime.rb
+++ b/lib/secure_mailing/smime.rb
@ -0,0 +1,6 @@
+class SecureMailing::SMIME < SecureMailing::Backend
+
+  def self.active?
+    Setting.get('smime_integration')
+  end
+end
--- a/lib/secure_mailing/smime/incoming.rb
+++ b/lib/secure_mailing/smime/incoming.rb
@ -0,0 +1,180 @@
+class SecureMailing::SMIME::Incoming < SecureMailing::Backend::Handler
+
+  EXPRESSION_MIME      = %r{application/(x-pkcs7|pkcs7)-mime}i.freeze
+  EXPRESSION_SIGNATURE = %r{application/(x-pkcs7|pkcs7)-signature}i.freeze
+
+  OPENSSL_PKCS7_VERIFY_FLAGS = OpenSSL::PKCS7::NOVERIFY | OpenSSL::PKCS7::NOINTERN
+
+  def initialize(mail)
+    @mail = mail
+    @content_type = @mail[:mail_instance].content_type
+  end
+
+  def process
+    return if !process?
+
+    initialize_article_preferences
+    decrypt
+    verify_signature
+    log
+  end
+
+  def initialize_article_preferences
+    article_preferences[:security] = {
+      type:       'S/MIME',
+      sign:       {
+        success: false,
+        comment: nil,
+      },
+      encryption: {
+        success: false,
+        comment: nil,
+      }
+    }
+  end
+
+  def article_preferences
+    @article_preferences ||= begin
+      key = 'x-zammad-article-preferences'.to_sym
+      @mail[ key ] ||= {}
+      @mail[ key ]
+    end
+  end
+
+  def process?
+    signed? || smime?
+  end
+
+  def signed?(content_type = @content_type)
+    EXPRESSION_SIGNATURE.match?(content_type)
+  end
+
+  def smime?(content_type = @content_type)
+    EXPRESSION_MIME.match?(content_type)
+  end
+
+  def decrypt
+    return if !smime?
+
+    success = false
+    comment = 'Unable to find private key to decrypt'
+    ::SMIMECertificate.where.not(private_key: [nil, '']).find_each do |cert|
+      key = OpenSSL::PKey::RSA.new(cert.private_key, cert.private_key_secret)
+
+      begin
+        decrypted_data = p7enc.decrypt(key, cert.parsed)
+      rescue
+        next
+      end
+
+      @mail[:mail_instance].header['Content-Type'] = nil
+      @mail[:mail_instance].header['Content-Disposition'] = nil
+      @mail[:mail_instance].header['Content-Transfer-Encoding'] = nil
+      @mail[:mail_instance].header['Content-Description'] = nil
+
+      new_raw_mail = "#{@mail[:mail_instance].header}#{decrypted_data}"
+
+      mail_new = Channel::EmailParser.new.parse(new_raw_mail)
+      mail_new.each do |local_key, local_value|
+        @mail[local_key] = local_value
+      end
+
+      success = true
+      comment = cert.subject
+      if cert.expired?
+        comment += " (Certificate #{cert.fingerprint} with start date #{cert.not_before_at} and end date #{cert.not_after_at} expired!)"
+      end
+
+      # overwrite content_type for signature checking
+      @content_type = @mail[:mail_instance].content_type
+      break
+    end
+
+    article_preferences[:security][:encryption] = {
+      success: success,
+      comment: comment,
+    }
+  end
+
+  def verify_signature
+    return if !signed?
+
+    success = false
+    comment = 'Unable to find certificate for verification'
+    ::SMIMECertificate.find_each do |cert|
+      verify_certs = []
+      verify_ca    = OpenSSL::X509::Store.new
+
+      if cert.parsed.issuer.to_s == cert.parsed.subject.to_s
+        verify_ca.add_cert(cert.parsed)
+
+        # CA
+        verify_certs = p7enc.certificates.select do |message_cert|
+          message_cert.issuer.to_s == cert.parsed.subject.to_s && verify_ca.verify(message_cert)
+        end
+      else
+
+        # normal
+        verify_certs.push(cert.parsed)
+      end
+
+      success = p7enc.verify(verify_certs, verify_ca, nil, OPENSSL_PKCS7_VERIFY_FLAGS)
+      next if !success
+
+      comment = cert.subject
+      if cert.expired?
+        comment += " (Certificate #{cert.fingerprint} with start date #{cert.not_before_at} and end date #{cert.not_after_at} expired!)"
+      end
+      break
+    rescue => e
+      success = false
+      comment = e.message
+    end
+
+    if success
+      @mail[:attachments].delete_if do |attachment|
+        signed?(attachment.dig(:preferences, 'Content-Type'))
+      end
+    end
+
+    article_preferences[:security][:sign] = {
+      success: success,
+      comment: comment,
+    }
+  end
+
+  def p7enc
+    OpenSSL::PKCS7.read_smime(@mail[:raw])
+  end
+
+  def log
+    %i[sign encryption].each do |action|
+      result = article_preferences[:security][action]
+      next if result.blank?
+
+      if result[:success]
+        status = 'success'
+      elsif result[:comment].blank?
+        # means not performed
+        next
+      else
+        status = 'failed'
+      end
+
+      HttpLog.create(
+        direction:     'in',
+        facility:      'S/MIME',
+        url:           "#{@mail[:from]} -> #{@mail[:to]}",
+        status:        status,
+        ip:            nil,
+        request:       {
+          message_id: @mail[:message_id],
+        },
+        response:      article_preferences[:security],
+        method:        action,
+        created_by_id: 1,
+        updated_by_id: 1,
+      )
+    end
+  end
+end
--- a/lib/secure_mailing/smime/outgoing.rb
+++ b/lib/secure_mailing/smime/outgoing.rb
@ -0,0 +1,84 @@
+class SecureMailing::SMIME::Outgoing < SecureMailing::Backend::Handler
+
+  def initialize(mail, security)
+    @mail     = mail
+    @security = security
+  end
+
+  def process
+    return if !process?
+
+    if @security[:sign][:success] && @security[:encryption][:success]
+      processed = encrypt(signed)
+      log('sign', 'success')
+      log('encryption', 'success')
+    elsif @security[:sign][:success]
+      processed = Mail.new(signed)
+      log('sign', 'success')
+    elsif @security[:encryption][:success]
+      processed = encrypt(@mail.encoded)
+      log('encryption', 'success')
+    end
+
+    overwrite_mail(processed)
+  end
+
+  def process?
+    return false if @security.blank?
+    return false if @security[:type] != 'S/MIME'
+
+    @security[:sign][:success] || @security[:encryption][:success]
+  end
+
+  def overwrite_mail(processed)
+    @mail.body = nil
+    @mail.body = processed.body.encoded
+
+    @mail.content_disposition       = processed.content_disposition
+    @mail.content_transfer_encoding = processed.content_transfer_encoding
+    @mail.content_type              = processed.content_type
+  end
+
+  def signed
+    from       = @mail.from.first
+    cert_model = SMIMECertificate.for_sender_email_address(from)
+    raise "Unable to find ssl private key for '#{from}'" if !cert_model
+    raise "Expired certificate for #{from} (fingerprint #{cert_model.fingerprint}) with #{cert_model.not_before_at} to #{cert_model.not_after_at}" if !@security[:sign][:allow_expired] && cert_model.expired?
+
+    private_key = OpenSSL::PKey::RSA.new(cert_model.private_key, cert_model.private_key_secret)
+    OpenSSL::PKCS7.write_smime(OpenSSL::PKCS7.sign(cert_model.parsed, private_key, @mail.encoded, [], OpenSSL::PKCS7::DETACHED))
+  rescue => e
+    log('sign', 'failed', e.message)
+    raise
+  end
+
+  def encrypt(data)
+    certificates = SMIMECertificate.for_recipipent_email_addresses!(@mail.to)
+    expired_cert = certificates.detect(&:expired?)
+    raise "Expired certificates for cert with #{expired_cert.not_before_at} to #{expired_cert.not_after_at}" if !@security[:encryption][:allow_expired] && expired_cert.present?
+
+    Mail.new(OpenSSL::PKCS7.write_smime(OpenSSL::PKCS7.encrypt(certificates.map(&:parsed), data, cipher)))
+  rescue => e
+    log('encryption', 'failed', e.message)
+    raise
+  end
+
+  def cipher
+    @cipher ||= OpenSSL::Cipher.new('AES-128-CBC')
+  end
+
+  def log(action, status, error = nil)
+    HttpLog.create(
+      direction:     'out',
+      facility:      'S/MIME',
+      url:           "#{@mail[:from]} -> #{@mail[:to]}",
+      status:        status,
+      ip:            nil,
+      request:       @security,
+      response:      { error: error },
+      method:        action,
+      created_by_id: 1,
+      updated_by_id: 1,
+    )
+  end
+end
--- a/lib/secure_mailing/smime/retry.rb
+++ b/lib/secure_mailing/smime/retry.rb
@ -0,0 +1,91 @@
+class SecureMailing::SMIME::Retry < SecureMailing::Backend::Handler
+
+  def initialize(article)
+    @article = article
+  end
+
+  def process
+    return existing_result if already_processed?
+
+    save_result if retry_succeeded?
+    retry_result
+  end
+
+  def signature_checked?
+    @signature_checked ||= existing_result&.dig('sign', 'success') || false
+  end
+
+  def decrypted?
+    @decrypted ||= existing_result&.dig('encryption', 'success') || false
+  end
+
+  def already_processed?
+    signature_checked? && decrypted?
+  end
+
+  def existing_result
+    @article.preferences['security']
+  end
+
+  def mail
+    @mail ||= begin
+      raw_mail = @article.as_raw.store_file.content
+      Channel::EmailParser.new.parse(raw_mail).tap do |parsed|
+        SecureMailing.incoming(parsed)
+      end
+    end
+  end
+
+  def retry_result
+    @retry_result ||= mail['x-zammad-article-preferences']['security']
+  end
+
+  def signature_found?
+    return false if signature_checked?
+
+    retry_result['sign']['success']
+  end
+
+  def decryption_succeeded?
+    return false if decrypted?
+
+    retry_result['encryption']['success']
+  end
+
+  def retry_succeeded?
+    return true if signature_found?
+
+    decryption_succeeded?
+  end
+
+  def save_result
+    save_decrypted if decryption_succeeded?
+    @article.preferences['security'] = retry_result
+    @article.save!
+  end
+
+  def save_decrypted
+    @article.content_type = mail['content_type']
+    @article.body         = mail['body']
+
+    Store.remove(
+      object: 'Ticket::Article',
+      o_id:   @article.id,
+    )
+
+    mail[:attachments]&.each do |attachment|
+      filename = attachment[:filename].force_encoding('utf-8')
+      if !filename.force_encoding('UTF-8').valid_encoding?
+        filename = filename.utf8_encode(fallback: :read_as_sanitized_binary)
+      end
+      Store.add(
+        object:        'Ticket::Article',
+        o_id:          @article.id,
+        data:          attachment[:data],
+        filename:      filename,
+        preferences:   attachment[:preferences],
+        created_by_id: @article.created_by_id,
+      )
+    end
+  end
+end
--- a/public/assets/images/icons.svg
+++ b/public/assets/images/icons.svg
@ -555,6 +555,11 @@
    <g fill-rule="evenodd">
        <path d="M1 6v4h3l4 3V3L4 6zM11.293 8L9.146 5.854a.5.5 0 1 1 .708-.708L12 7.293l2.146-2.147a.5.5 0 0 1 .708.708L12.707 8l2.147 2.146a.5.5 0 0 1-.708.708L12 8.707l-2.146 2.147a.5.5 0 0 1-.708-.708L11.293 8z"/>
    </g>
+</symbol><symbol id="icon-not-signed" viewBox="0 0 14 14">
+    <title>
+        not-signed
+    </title>
+    <path d="M7.317.106c.03.023.058.049.082.077l1.155 1.385a.524.524 0 0 0 .534.166l1.787-.472a.513.513 0 0 1 .627.339c.01.035.017.071.018.108l.082 1.768a.489.489 0 0 0 .33.434l1.737.62a.48.48 0 0 1 .246.724l-1.023 1.477a.468.468 0 0 0 0 .536l1.023 1.477a.473.473 0 0 1-.144.673.52.52 0 0 1-.102.05l-1.737.62a.489.489 0 0 0-.33.435l-.082 1.768a.5.5 0 0 1-.531.465.532.532 0 0 1-.114-.018l-1.787-.472a.524.524 0 0 0-.534.166l-1.155 1.385a.526.526 0 0 1-.798 0l-1.155-1.385a.524.524 0 0 0-.534-.166l-1.787.472a.513.513 0 0 1-.627-.339.466.466 0 0 1-.018-.108l-.082-1.768a.489.489 0 0 0-.33-.434L.33 9.469a.48.48 0 0 1-.246-.724l1.023-1.477a.468.468 0 0 0 0-.536L.085 5.255a.473.473 0 0 1 .144-.673.52.52 0 0 1 .102-.05l1.737-.62a.489.489 0 0 0 .33-.435L2.48 1.71a.5.5 0 0 1 .531-.465.532.532 0 0 1 .114.018l1.787.472a.524.524 0 0 0 .534-.166L6.601.183a.526.526 0 0 1 .716-.077zm-2.903 3.55a.535.535 0 0 0-.757.758l2.598 2.598-2.557 2.574a.535.535 0 0 0 .76.754L7.012 7.77l2.573 2.573a.535.535 0 0 0 .757-.757L7.766 7.009l2.579-2.597a.535.535 0 1 0-.76-.754L7.01 6.252z" fill-rule="evenodd"/>
 </symbol><symbol id="icon-note" viewBox="0 0 16 16">
    <title>
        note
@ -716,6 +721,11 @@
        <path d="M13.21 8.62a1.602 1.602 0 0 1-1.59-1.61 1.604 1.604 0 0 1 1.6-1.59h.01c.427.003.827.172 1.127.476.3.304.463.707.46 1.134-.003.425-.17.826-.471 1.125-.301.3-.702.465-1.126.465h-.01M10 6.953a3.172 3.172 0 0 0 4.768 2.76l1.926 1.93.05.047a.37.37 0 0 0 .526 0l.621-.62a.375.375 0 0 0 0-.527l-.048-.05-1.93-1.93A3.17 3.17 0 0 0 13.191 3.8 3.177 3.177 0 0 0 10 6.953z" opacity=".5"/>
        <path d="M0 1c0-.552.449-1 1.007-1h12.986C14.549 0 15 .444 15 1c0 .552-.449 1-1.007 1H1.007A1.001 1.001 0 0 1 0 1zm0 4c0-.552.446-1 .998-1h7.004C8.553 4 9 4.444 9 5c0 .552-.446 1-.998 1H.998A.996.996 0 0 1 0 5zm0 4c0-.552.446-1 .998-1h7.004C8.553 8 9 8.444 9 9c0 .552-.446 1-.998 1H.998A.996.996 0 0 1 0 9zm0 4c0-.552.449-1 1.007-1h12.986c.556 0 1.007.444 1.007 1 0 .552-.449 1-1.007 1H1.007A1.001 1.001 0 0 1 0 13z"/>
    </g>
+</symbol><symbol id="icon-signed" viewBox="0 0 14 14">
+    <title>
+        signed
+    </title>
+    <path d="M7.317.106c.03.023.058.049.082.077l1.155 1.385a.524.524 0 0 0 .534.166l1.787-.472a.513.513 0 0 1 .627.339c.01.035.017.071.018.108l.082 1.768a.489.489 0 0 0 .33.434l1.737.62a.48.48 0 0 1 .246.724l-1.023 1.477a.468.468 0 0 0 0 .536l1.023 1.477a.473.473 0 0 1-.144.673.52.52 0 0 1-.102.05l-1.737.62a.489.489 0 0 0-.33.435l-.082 1.768a.5.5 0 0 1-.531.465.532.532 0 0 1-.114-.018l-1.787-.472a.524.524 0 0 0-.534.166l-1.155 1.385a.526.526 0 0 1-.798 0l-1.155-1.385a.524.524 0 0 0-.534-.166l-1.787.472a.513.513 0 0 1-.627-.339.466.466 0 0 1-.018-.108l-.082-1.768a.489.489 0 0 0-.33-.434L.33 9.469a.48.48 0 0 1-.246-.724l1.023-1.477a.468.468 0 0 0 0-.536L.085 5.255a.473.473 0 0 1 .144-.673.52.52 0 0 1 .102-.05l1.737-.62a.489.489 0 0 0 .33-.435L2.48 1.71a.5.5 0 0 1 .531-.465.532.532 0 0 1 .114.018l1.787.472a.524.524 0 0 0 .534-.166L6.601.183a.526.526 0 0 1 .716-.077zM10.6 4S7.804 5.156 5.638 7.868l-.087-.086c-.256-.251-1.024-.98-1.498-1.189-.576-.253-.953.615-.953.615s1.432 1.25 3.062 2.928C7.963 6.528 10.6 4.708 10.6 4.708V4z" fill-rule="evenodd"/>
 </symbol><symbol id="icon-signout" viewBox="0 0 15 19">
    <title>
        signout
--- a/public/assets/images/icons/not-signed.svg
+++ b/public/assets/images/icons/not-signed.svg
@ -0,0 +1,9 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<svg width="14px" height="14px" viewBox="0 0 14 14" version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
+    <!-- Generator: Sketch 61.1 (89650) - https://sketch.com -->
+    <title>not-signed</title>
+    <desc>Created with Sketch.</desc>
+    <g id="not-signed" stroke="none" stroke-width="1" fill="none" fill-rule="evenodd">
+        <path d="M7.31730677,0.105840662 C7.34739634,0.128701418 7.37467735,0.154740401 7.39862853,0.183460083 L8.55352341,1.56828587 C8.68077561,1.72087303 8.89122527,1.78613917 9.08814095,1.73408525 L10.8752764,1.26166273 C11.1464562,1.18997736 11.4271753,1.34169118 11.50228,1.60052501 C11.5125448,1.63590076 11.5185802,1.67227207 11.5202709,1.708944 L11.6017946,3.47721668 C11.6107773,3.67205396 11.7408424,3.84292293 11.9322064,3.91128508 L13.6689575,4.53171518 C13.932492,4.62585921 14.0661698,4.90608871 13.9675352,5.15762529 C13.9540545,5.19200369 13.936539,5.22481473 13.9153234,5.25543147 L12.8923367,6.73173097 C12.7796188,6.89439717 12.7796188,7.10560283 12.8923367,7.26826903 L13.9153234,8.74456853 C14.0705514,8.96858215 14.0061276,9.27028919 13.7714289,9.41845008 C13.7393517,9.43869976 13.7049757,9.45541782 13.6689575,9.46828482 L11.9322064,10.0887149 C11.7408424,10.1570771 11.6107773,10.327946 11.6017946,10.5227833 L11.5202709,12.291056 C11.5079005,12.5593736 11.2699828,12.7673164 10.9888668,12.7555091 C10.9504457,12.7538954 10.9123395,12.7481348 10.8752764,12.7383373 L9.08814095,12.2659148 C8.89122527,12.2138608 8.68077561,12.279127 8.55352341,12.4317141 L7.39862853,13.8165399 C7.22338484,14.0266733 6.90284969,14.0614247 6.68269323,13.8941593 C6.65260366,13.8712986 6.62532265,13.8452596 6.60137147,13.8165399 L5.44647659,12.4317141 C5.31922439,12.279127 5.10877473,12.2138608 4.91185905,12.2659148 L3.1247236,12.7383373 C2.85354375,12.8100226 2.5728247,12.6583088 2.49772005,12.399475 C2.48745522,12.3640992 2.4814198,12.3277279 2.47972909,12.291056 L2.39820537,10.5227833 C2.38922267,10.327946 2.25915763,10.1570771 2.06779356,10.0887149 L0.331042537,9.46828482 C0.0675080262,9.37414079 -0.0661697902,9.09391129 0.0324647774,8.84237471 C0.0459455161,8.80799631 0.0634609997,8.77518527 0.0846765586,8.74456853 L1.10766329,7.26826903 C1.22038117,7.10560283 1.22038117,6.89439717 1.10766329,6.73173097 L0.0846765586,5.25543147 C-0.0705513951,5.03141785 -0.00612759356,4.72971081 0.228571147,4.58154992 C0.260648262,4.56130024 0.295024334,4.54458218 0.331042537,4.53171518 L2.06779356,3.91128508 C2.25915763,3.84292293 2.38922267,3.67205396 2.39820537,3.47721668 L2.47972909,1.708944 C2.4920995,1.44062639 2.73001721,1.23268363 3.01113319,1.24449085 C3.04955431,1.24610459 3.08766048,1.25186524 3.1247236,1.26166273 L4.91185905,1.73408525 C5.10877473,1.78613917 5.31922439,1.72087303 5.44647659,1.56828587 L6.60137147,0.183460083 C6.77661516,-0.0266733112 7.09715031,-0.0614247095 7.31730677,0.105840662 Z M4.41361229,3.65675097 C4.20461083,3.44774968 3.8657525,3.44774968 3.6567511,3.65675097 C3.44774963,3.86575281 3.44774963,4.20461113 3.6567511,4.41361243 L3.6567511,4.41361243 L6.25490847,7.01176976 L3.69831796,9.58623834 C3.49004601,9.79596695 3.49122667,10.1348231 3.70095507,10.343095 C3.91068347,10.5513674 4.24953976,10.5501862 4.45781171,10.3404581 L4.45781171,10.3404581 L7.01177432,7.7686355 L9.58491757,10.341779 C9.79391887,10.5507803 10.1327772,10.5507803 10.341779,10.341779 C10.5507803,10.1327777 10.5507803,9.79391934 10.341779,9.58491751 L10.341779,9.58491751 L7.76599841,7.0091372 L10.3448103,4.41229161 C10.5530827,4.20256299 10.5519015,3.86370681 10.3421735,3.65543496 C10.1324449,3.44716312 9.79358867,3.44834373 9.58531682,3.6580718 L9.58531682,3.6580718 L7.00913256,6.25227146 Z" id="Combined-Shape" fill="#50E3C2"></path>
+    </g>
+</svg>
--- a/public/assets/images/icons/signed.svg
+++ b/public/assets/images/icons/signed.svg
@ -0,0 +1,9 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<svg width="14px" height="14px" viewBox="0 0 14 14" version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
+    <!-- Generator: Sketch 61.1 (89650) - https://sketch.com -->
+    <title>signed</title>
+    <desc>Created with Sketch.</desc>
+    <g id="signed" stroke="none" stroke-width="1" fill="none" fill-rule="evenodd">
+        <path d="M7.31730677,0.105840662 C7.34739634,0.128701418 7.37467735,0.154740401 7.39862853,0.183460083 L8.55352341,1.56828587 C8.68077561,1.72087303 8.89122527,1.78613917 9.08814095,1.73408525 L10.8752764,1.26166273 C11.1464562,1.18997736 11.4271753,1.34169118 11.50228,1.60052501 C11.5125448,1.63590076 11.5185802,1.67227207 11.5202709,1.708944 L11.6017946,3.47721668 C11.6107773,3.67205396 11.7408424,3.84292293 11.9322064,3.91128508 L13.6689575,4.53171518 C13.932492,4.62585921 14.0661698,4.90608871 13.9675352,5.15762529 C13.9540545,5.19200369 13.936539,5.22481473 13.9153234,5.25543147 L12.8923367,6.73173097 C12.7796188,6.89439717 12.7796188,7.10560283 12.8923367,7.26826903 L13.9153234,8.74456853 C14.0705514,8.96858215 14.0061276,9.27028919 13.7714289,9.41845008 C13.7393517,9.43869976 13.7049757,9.45541782 13.6689575,9.46828482 L11.9322064,10.0887149 C11.7408424,10.1570771 11.6107773,10.327946 11.6017946,10.5227833 L11.5202709,12.291056 C11.5079005,12.5593736 11.2699828,12.7673164 10.9888668,12.7555091 C10.9504457,12.7538954 10.9123395,12.7481348 10.8752764,12.7383373 L9.08814095,12.2659148 C8.89122527,12.2138608 8.68077561,12.279127 8.55352341,12.4317141 L7.39862853,13.8165399 C7.22338484,14.0266733 6.90284969,14.0614247 6.68269323,13.8941593 C6.65260366,13.8712986 6.62532265,13.8452596 6.60137147,13.8165399 L5.44647659,12.4317141 C5.31922439,12.279127 5.10877473,12.2138608 4.91185905,12.2659148 L3.1247236,12.7383373 C2.85354375,12.8100226 2.5728247,12.6583088 2.49772005,12.399475 C2.48745522,12.3640992 2.4814198,12.3277279 2.47972909,12.291056 L2.39820537,10.5227833 C2.38922267,10.327946 2.25915763,10.1570771 2.06779356,10.0887149 L0.331042537,9.46828482 C0.0675080262,9.37414079 -0.0661697902,9.09391129 0.0324647774,8.84237471 C0.0459455161,8.80799631 0.0634609997,8.77518527 0.0846765586,8.74456853 L1.10766329,7.26826903 C1.22038117,7.10560283 1.22038117,6.89439717 1.10766329,6.73173097 L0.0846765586,5.25543147 C-0.0705513951,5.03141785 -0.00612759356,4.72971081 0.228571147,4.58154992 C0.260648262,4.56130024 0.295024334,4.54458218 0.331042537,4.53171518 L2.06779356,3.91128508 C2.25915763,3.84292293 2.38922267,3.67205396 2.39820537,3.47721668 L2.47972909,1.708944 C2.4920995,1.44062639 2.73001721,1.23268363 3.01113319,1.24449085 C3.04955431,1.24610459 3.08766048,1.25186524 3.1247236,1.26166273 L4.91185905,1.73408525 C5.10877473,1.78613917 5.31922439,1.72087303 5.44647659,1.56828587 L6.60137147,0.183460083 C6.77661516,-0.0266733112 7.09715031,-0.0614247095 7.31730677,0.105840662 Z M10.6,4 C10.6,4 7.80412273,5.15585215 5.63774444,7.86753754 L5.55140868,7.7819143 C5.29513787,7.53084111 4.52720714,6.80110202 4.05313247,6.5929648 C3.47747036,6.34022674 3.1,7.20839783 3.1,7.20839783 C3.1,7.20839783 4.53194541,8.45802624 6.16208587,10.1358979 C7.9633403,6.52815973 10.6,4.7076373 10.6,4.7076373 L10.6,4 Z" id="Combined-Shape" fill="#50E3C2"></path>
+    </g>
+</svg>
--- a/spec/factories/smime_certificate.rb
+++ b/spec/factories/smime_certificate.rb
@ -0,0 +1,17 @@
+FactoryBot.define do
+  factory :smime_certificate do
+    created_at         { Time.zone.now }
+    updated_at         { Time.zone.now }
+
+    transient do
+      fixture { nil }
+    end
+
+    public_key { File.read( Rails.root.join("spec/fixtures/smime/#{fixture}.crt") ) if fixture }
+
+    trait :with_private do
+      private_key { File.read( Rails.root.join("spec/fixtures/smime/#{fixture}.key") ) }
+      private_key_secret { File.read( Rails.root.join("spec/fixtures/smime/#{fixture}.secret") ).strip! }
+    end
+  end
+end
--- a/spec/factories/template.rb
+++ b/spec/factories/template.rb
@ -17,12 +17,13 @@ FactoryBot.define do
    trait :dummy_data do
      options do
        {
-          'formSenderType' => sender_type,
-          'title'          => title,
-          'body'           => body,
-          'customer_id'    => customer.id,
-          'group_id'       => group.id,
-          'owner_id'       => owner.id,
+          'formSenderType'         => sender_type,
+          'title'                  => title,
+          'body'                   => body,
+          'customer_id'            => customer.id,
+          'customer_id_completion' => "#{customer.firstname} #{customer.lastname} <#{customer.email}>",
+          'group_id'               => group.id,
+          'owner_id'               => owner.id,
        }
      end
    end
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.crt
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.crt
@ -0,0 +1,37 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.csr
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.key
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,897152EBDB085F8EFC4E413FBF5A35FD
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.secret
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/ca.crt
+++ b/spec/fixtures/smime/ca.crt
@ -0,0 +1,35 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
--- a/spec/fixtures/smime/ca.key
+++ b/spec/fixtures/smime/ca.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,C883629DF6D2EB2F339DA0E9DDE3A287
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/ca.secret
+++ b/spec/fixtures/smime/ca.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/expiredca.crt
+++ b/spec/fixtures/smime/expiredca.crt
@ -0,0 +1,35 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
--- a/spec/fixtures/smime/expiredca.key
+++ b/spec/fixtures/smime/expiredca.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,AFFF2A7AF6117991109A4B9D75D38008
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/expiredca.secret
+++ b/spec/fixtures/smime/expiredca.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/expiredsmime1@example.com.crt
+++ b/spec/fixtures/smime/expiredsmime1@example.com.crt
@ -0,0 +1,37 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/expiredsmime1@example.com.csr
+++ b/spec/fixtures/smime/expiredsmime1@example.com.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/expiredsmime1@example.com.key
+++ b/spec/fixtures/smime/expiredsmime1@example.com.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,8CE77F705A91FC4378059C551C7C5A05
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/expiredsmime1@example.com.secret
+++ b/spec/fixtures/smime/expiredsmime1@example.com.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/expiredsmime2@example.com.crt
+++ b/spec/fixtures/smime/expiredsmime2@example.com.crt
@ -0,0 +1,37 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+BDFPN1E+9oEkHcUwIjAKBggrBgEFBQcDBKAUBggrBgEFBQcDAgYIKwYBBQUHAwE=
+-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/expiredsmime2@example.com.csr
+++ b/spec/fixtures/smime/expiredsmime2@example.com.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
+MIIE6DCCAtACAQAwgaIxKDAmBgkqhkiG9w0BCQEWGWV4cGlyZWRzbWltZTJAZXhh
+bXBsZS5jb20xCzAJBgNVBAYTAkRFMQ8wDQYDVQQIDAZCZXJsaW4xDzANBgNVBAcM
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+hLPOcHKMoBEygeCn
+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/expiredsmime2@example.com.key
+++ b/spec/fixtures/smime/expiredsmime2@example.com.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,2D01520A669DCCAAC31310846FD3F95A
+
+uVTH48B5k3TxkQgfo3lXllNxXLICC5UZXv6znRxk35fJD7PnDpeOMDijlW7S4+gi
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/expiredsmime2@example.com.secret
+++ b/spec/fixtures/smime/expiredsmime2@example.com.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/generate/Dockerfile
+++ b/spec/fixtures/smime/generate/Dockerfile
@ -0,0 +1,21 @@
+FROM alpine
+
+# faketime dependencies to generate outdated certificates
+# see: https://github.com/trajano/alpine-libfaketime#with-simple-command-line-apps
+COPY --from=trajano/alpine-libfaketime  /faketime.so /lib/faketime.so
+ENV LD_PRELOAD=/lib/faketime.so
+ENV CERT_DIR "/etc/ssl/certs"
+
+# install openssl
+RUN apk add --update openssl && \
+    rm -rf /var/cache/apk/*
+
+# move base files to the container
+COPY config/* /
+COPY docker-entrypoint.sh /
+
+# enable volume to generate certificates into the hosts FS
+VOLUME ["$CERT_DIR"]
+
+# start
+ENTRYPOINT ["/docker-entrypoint.sh"]
--- a/spec/fixtures/smime/generate/README.md
+++ b/spec/fixtures/smime/generate/README.md
@ -0,0 +1,6 @@
+# Zammad S/MIME test certificate generation
+
+This folder contains a `docker` image and the required files to generate various S/MIME certificates for testing purposes. These contain CA certificates as regular certificates (1). There is one special certificate that is for multiple emails at once (2). Additionally some already expired CA and certificates are generated (3).
+For the CA there are `.key` and `.crt` files. For the certificates the `.key`, `.crt` and `.csr` are generated. Additionally a `.secret` file is added that contains the corresponding pass phrase.
+
+These are easily generated by executing the `run.sh` file. There is nothing more to it except of having `docker` installed and running.
--- a/spec/fixtures/smime/generate/config/config.cnf
+++ b/spec/fixtures/smime/generate/config/config.cnf
@ -0,0 +1,8 @@
+[smime]
+basicConstraints = CA:FALSE
+keyUsage = nonRepudiation, digitalSignature, keyEncipherment
+subjectKeyIdentifier = hash
+#authorityKeyIdentifier = keyid:always,issuer
+authorityKeyIdentifier = keyid,issuer
+subjectAltName = email:copy
+extendedKeyUsage = emailProtection
--- a/spec/fixtures/smime/generate/config/double.cnf
+++ b/spec/fixtures/smime/generate/config/double.cnf
@ -0,0 +1,15 @@
+[ smime ]
+basicConstraints = CA:FALSE
+keyUsage = nonRepudiation, digitalSignature, keyEncipherment
+subjectKeyIdentifier = hash
+#authorityKeyIdentifier = keyid:always,issuer
+authorityKeyIdentifier = keyid,issuer
+extendedKeyUsage = emailProtection
+subjectAltName=@alt_names
+
+[alt_names]
+IP.1 = 192.168.0.23
+IP.2 = 192.168.0.42
+email.1 = smimedouble@example.com
+email.2 = smimedouble@example.de
+otherName = 1.2.3.4;UTF8:some other identifier
--- a/spec/fixtures/smime/generate/config/pass.secret
+++ b/spec/fixtures/smime/generate/config/pass.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/generate/docker-entrypoint.sh
+++ b/spec/fixtures/smime/generate/docker-entrypoint.sh
@ -0,0 +1,104 @@
+#!/bin/sh
+
+echo "Zammad S/MIME test certificate generation"
+
+if [[ ! -e "$CERT_DIR/ca.key" ]] || [[ ! -e "$CERT_DIR/ca.crt" ]]
+then
+  echo "Generating ca.key"
+  openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/ca.key 4096
+
+  echo "Generating ca.crt"
+  openssl req -new -x509 -days 73000 -key $CERT_DIR/ca.key -passin file:pass.secret -out $CERT_DIR/ca.crt -subj "/emailAddress=ca@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
+
+  echo "Generating ca.secret"
+  cp pass.secret $CERT_DIR/ca.secret
+fi
+
+for EMAIL_ADDRESS in smime1@example.com smime2@example.com smime3@example.com smimedouble@example.com CaseInsenstive@eXample.COM
+do
+  if [[ ! -e "$CERT_DIR/$EMAIL_ADDRESS.crt" ]]
+  then
+    echo "Generating $EMAIL_ADDRESS.key"
+    openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/$EMAIL_ADDRESS.key 4096
+
+    echo "Generating $EMAIL_ADDRESS.csr (certificate signing request)"
+    openssl req -new -key $CERT_DIR/$EMAIL_ADDRESS.key -passin file:pass.secret -out $CERT_DIR/$EMAIL_ADDRESS.csr -subj "/emailAddress=$EMAIL_ADDRESS/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
+
+    echo "Generating $EMAIL_ADDRESS.crt (certificate)"
+
+    if [ "$EMAIL_ADDRESS" != "smimedouble@example.com" ]
+    then
+      extfile="config.cnf"
+    else
+      # special config that contains two email addresses in one certificate
+      extfile="double.cnf"
+    fi
+
+    openssl x509 -req \
+        -days 73000 \
+        -in $CERT_DIR/$EMAIL_ADDRESS.csr \
+        -CA $CERT_DIR/ca.crt \
+        -CAkey $CERT_DIR/ca.key \
+        -out $CERT_DIR/$EMAIL_ADDRESS.crt \
+        -addtrust emailProtection \
+        -addreject clientAuth \
+        -addreject serverAuth \
+        -trustout \
+        -CAcreateserial -CAserial /tmp/ca.seq \
+        -extensions smime \
+        -extfile "$extfile" \
+        -passin file:pass.secret
+
+    echo "Generating $EMAIL_ADDRESS.secret"
+    cp pass.secret $CERT_DIR/$EMAIL_ADDRESS.secret
+  fi
+done
+
+echo "Generating expired"
+FAKETIME=-10y date
+
+if [[ ! -e "$CERT_DIR/expiredca.key" ]] || [[ ! -e "$CERT_DIR/expiredca.crt" ]]
+then
+  echo "Generating expiredca.key"
+  FAKETIME=-10y openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/expiredca.key 4096
+
+  echo "Generating expiredca.crt"
+  FAKETIME=-10y openssl req -new -x509 -days 1 -key $CERT_DIR/expiredca.key -passin file:pass.secret -out $CERT_DIR/expiredca.crt -subj "/emailAddress=expiredca@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
+
+  echo "Generating expiredca.secret"
+  cp pass.secret $CERT_DIR/expiredca.secret
+fi
+
+for EMAIL_ADDRESS in expiredsmime1@example.com expiredsmime2@example.com
+do
+  if [[ ! -e "$CERT_DIR/$EMAIL_ADDRESS.crt" ]]
+  then
+    echo "Generating $EMAIL_ADDRESS.key"
+    FAKETIME=-10y openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/$EMAIL_ADDRESS.key 4096
+
+    echo "Generating $EMAIL_ADDRESS.csr (certificate signing request)"
+    FAKETIME=-10y openssl req -new -key $CERT_DIR/$EMAIL_ADDRESS.key -passin file:pass.secret -out $CERT_DIR/$EMAIL_ADDRESS.csr -subj "/emailAddress=$EMAIL_ADDRESS/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
+
+    echo "Generating $EMAIL_ADDRESS.crt (certificate)"
+    FAKETIME=-10y openssl x509 -req \
+        -days 1 \
+        -in $CERT_DIR/$EMAIL_ADDRESS.csr \
+        -CA $CERT_DIR/expiredca.crt \
+        -CAkey $CERT_DIR/expiredca.key \
+        -out $CERT_DIR/$EMAIL_ADDRESS.crt \
+        -addtrust emailProtection \
+        -addreject clientAuth \
+        -addreject serverAuth \
+        -trustout \
+        -CAcreateserial -CAserial /tmp/expiredca.seq \
+        -extensions smime \
+        -extfile config.cnf \
+        -passin file:pass.secret
+
+    echo "Generating $EMAIL_ADDRESS.secret"
+    cp pass.secret $CERT_DIR/$EMAIL_ADDRESS.secret
+  fi
+done
+
+# run command passed to docker run
+exec "$@"
--- a/spec/fixtures/smime/generate/run.sh
+++ b/spec/fixtures/smime/generate/run.sh
@ -0,0 +1,9 @@
+#!/bin/bash
+
+set -o errexit
+set -o pipefail
+
+docker build --no-cache -t zammad/smime-test-certificates:latest .
+
+docker run --rm -v `pwd`/../:/etc/ssl/certs zammad/smime-test-certificates:latest
+
--- a/spec/fixtures/smime/oldca.crt
+++ b/spec/fixtures/smime/oldca.crt
@ -0,0 +1,35 @@
+-----BEGIN CERTIFICATE-----
+MIIGFzCCA/+gAwIBAgIUMmCv8hoMpL1DxnfbdnB7B8toiJYwDQYJKoZIhvcNAQEL
+BQAwgZoxIDAeBgkqhkiG9w0BCQEWEW9sZGNhQGV4YW1wbGUuY29tMQswCQYDVQQG
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+-----END CERTIFICATE-----
--- a/spec/fixtures/smime/oldca.key
+++ b/spec/fixtures/smime/oldca.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,1B90035BC983D129D9910AA0D912DDE2
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/oldca.secret
+++ b/spec/fixtures/smime/oldca.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/oldsmime1@example.com.crt
+++ b/spec/fixtures/smime/oldsmime1@example.com.crt
@ -0,0 +1,37 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/oldsmime1@example.com.csr
+++ b/spec/fixtures/smime/oldsmime1@example.com.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/oldsmime1@example.com.key
+++ b/spec/fixtures/smime/oldsmime1@example.com.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,075058C49FC97E93DC2A6598E450A08C
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/oldsmime1@example.com.secret
+++ b/spec/fixtures/smime/oldsmime1@example.com.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/oldsmime2@example.com.crt
+++ b/spec/fixtures/smime/oldsmime2@example.com.crt
@ -0,0 +1,37 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/oldsmime2@example.com.csr
+++ b/spec/fixtures/smime/oldsmime2@example.com.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/oldsmime2@example.com.key
+++ b/spec/fixtures/smime/oldsmime2@example.com.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,422646293BBDFBBD651E2D08160A9FE1
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/oldsmime2@example.com.secret
+++ b/spec/fixtures/smime/oldsmime2@example.com.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/smime1@example.com.crt
+++ b/spec/fixtures/smime/smime1@example.com.crt
@ -0,0 +1,37 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/smime1@example.com.csr
+++ b/spec/fixtures/smime/smime1@example.com.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/smime1@example.com.key
+++ b/spec/fixtures/smime/smime1@example.com.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,C02E7FD1CD5C829F69D753D19B84384A
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/smime1@example.com.secret
+++ b/spec/fixtures/smime/smime1@example.com.secret
@ -0,0 +1 @@
+1234
--- a/spec/fixtures/smime/smime2@example.com.crt
+++ b/spec/fixtures/smime/smime2@example.com.crt
@ -0,0 +1,37 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/smime2@example.com.csr
+++ b/spec/fixtures/smime/smime2@example.com.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/smime2@example.com.key
+++ b/spec/fixtures/smime/smime2@example.com.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,E635B30D63879480FEACF294E0B57BB7
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/smime2@example.com.secret
+++ b/spec/fixtures/smime/smime2@example.com.secret
@ -0,0 +1 @@
+1234
--- a/Show more
+++ b/Show more